If the guide helped you in any way then please use the thumbs up, favourite buttons and follow my achievement related curator which telling you the perfection time of games, difficulty of perfection, DLC/MP requirements. Games also ordered to lists based on their completion times:

https://steamproxy.com/steamstore/curator/30168383-Average-Achievement-Hunter/


DLC

There are no DLC related achievements in this game but one achievements is bugged, it misscount the locomotoive counts so you still need the West DLC for 1 achievement.

Completion time and difficulty

It takes about 40-50 hours to get all achievements in this game. It isn't hard to do so, just grind required. You can play the game on any difficulty, but you can set up difficulty only at the beginning, you can't change it later.

First Savings
Collect $10,000

Financial Sustainability
Collect $25,000

Tycoon
People owning a bankroll of $50,000 are hugely respected among businessmen. Become one of them!

Piggybanker
Earn 1000$ worth of interest on your bank deposit.

Swimming in Money
Obtain one million dollar turnover through all sessions of the game.

You shouldn't have problem to get these achievements. You will easily get more money than this, you will even get to a point where the bank interest will be more than 1mill if you keep putting in money as the bank offers insane amount of interest for short time, like 10-13% for only 45days.

Unhindered
Obtain licenses to travel all routes in the game.

You need to unlock railways between cities with so called licences what you can buy for more. Just click on the lock on the map, pay the many and you can now use travel on that railroad. Unlock all paths on map to get this achievement.

1, 2, 3... Sold!
Win an auction.

Monthly, or like every 45days there is an auction event. If it happens go to the affected city, you need have a +40 reputation there and join the auction at the city hall. Win it by the first time and the achievement is yours.

Real Estate Baron
Win 10 auctions for real estate properties.

Do the previous ten times.

Conglomerate
Be in possession of a Coal mine, Steel factory, Tools factory and Weapon factory simultaneously.

Standard Oil
Purchase 3 oil wells.

Conglomerate and Standard oil are both very annoying achievements. It is random what kind of auction will be out there and you need to own these buildings at the same time. Standard oil require you to own 3 oil wells at the same time too, not just to purchase it 3 times. This is important to mention as there are so called fire events which destroy your properties in the affected city. Please keep in mind that game ends permanently once you finish the campaign so the best way to get these achievements is, that you get to a point where you have 51% shares but you dont go to talk with your enemy. You can do this if you own the West DLC as the game progressing to the DLC story then. Once in DLC you can keep playing indefinietly if you dont open the factory. So once at these stages just let time pass by setting time option that time should stop at next event and keep time going until you have the required buildings, Still save sometimes and reload if an unwanted fire event occurs.

Dreamrider
Purchase Sierra 4-6-0 locomotive.

This is the fastest train available in the game and will be available several years after the game start. You will need this for the extrem grind 1mill miles travaled achievement.

Railbuff
Gather a complete collection of all locomotives.

This achievement is bugged right now and you need to get +1 locomotives to get the achievement, which means that you need to have the West DLC for the locomotive purchasable there. For a complete checklist, here are the available locomotives:

General 4-4-0
DeWitt 0-4-0
John Bull 4-2-0
Cumberland Pioneer 2-2-2T
Chicago Pioneer 4-2-0
Forney 0-4-4T
Sierra 4-6-0
Mogul 2-6-0
Memnon (West DLC) 0-8-0

Pullman Car
Convey 25 passengers.

There are three main type of quest. One of it is to deliver passangers to some other station. You can pick up these quests to either click on the NPCs with blue name or click on the train station, which provide a much better overview about possible passanger quests. Do this 25 times and this achievement is yours. Trivial achievement.

Man of Reliance
Complete 100 quests.

Trivial quest, 100 quests get finished pretty fast, deliver passangers, transport goods, hunt down wanted criminals, smuggle goods.

Logistician
Complete 50 requests to transport goods.

There are three main type of quest. One of it is to transport goods from one city to another, or eventually get supplies for the city where you pick up the quest. These kind of quests available in the city hall building.

Natural Born Courier
Deliver 15 letters to the post offices.

At the post offices you can do 2 things. Sign up to newspapers, so you will see the actual prices of the goods in the affected city from every other location and get mail delivery quest. These mail quests dont require any extra wagon so you can just travel with your locomotive for faster travel as reward is based on the speed of your delivery.

Smuggler
Do 10 smuggling runs for the bootleggers in the saloon.

Some city has so called "Saloons", where bandits offering you quests. There are usually supply runs, you don't want that or smuggling, which is the required for this achievement. To smuggle you need to upgrade your cargo wagons else there will be 100% chance for authorities to find contrabands like weapons and alcohols as these banned in most of the cities. To decrease the fail chance even more add more cargos to your wagons, dont deliver only the contrabands, and, of course, save your game and reload if required.

Please keep in mind that being nice with bandits decrease city reputations just like union and confederate reputation, so dont do all 10 at the same time. Additional important information that you need to do this in one single game, so reloading ten times for the same quest wont count, you need do 10 different one in the same playthrough.

Bounty Hunter
Enforce law and order. Kill 7 wanted criminals.

Just like for Smuggler you need to do this in a single playthrough and you need to do on 7 different occasions. Also an important information that you actually need to do 7 wanted quests, so not the kill counts. Long Wanted quests are VERY rare, so this is an annoying quests. There are wanted criminals on map sometimes, but they come and go very fast so here is a trick how to get such quests:
Go to Cincinnati or St. Louis, as both cities has 5 path to leave or enter. Set the time options to 24h. Keep time going, each time 24h at once and keep it going until near one of the path a human figure shows up which is in a black cloth. If it is not in black then that one is just a simple bandit whcih not WANTED yet. Once you see that wanted criminal go to the city hall, pick up the quest and travel on the affected path with your crew. Once killed turn in the quest and wait for the next wanted criminal. I suggest to wait for Sierra train for this as these wanted criminal really stay there only for like 24h and dont use other wagons than the one which carry crew members.

Jessie James
Find yourself on a wanted poster.

Trivial achievement and you will get it while going for +100 union/confederate achievements. Just get -100 reputation in one of the city and the achievement is yours.

Faithful Confederate
Earn +100 of Confederate Army's trust

Union's Ally
Earn +100 of Union's faith

I believe you can get only one of it in a single playthrough but it dont require a lot of time to get the other one in a brand new game.

How to get it?:

First of all start to finsih quests only for union or confederate cities. Dont finish unique missions for reputation as you need to get the final reputations via those. It is nearly impossible to get higher than +70-80 without those (not sure it is true, that is my own experience). Max out union/confederate cities with passanger/cargo delivery quest, try to avoid quests which require a delivery to a city which belong to another faction. Then attack union/confederate bases. Once close, consider to get the last points via there unique missions: (please keep in mind i not wrote up all possible quests, if you play the game and you found others then please share it via comments)

Main campaign quest: There will be a point where you need to deliver a wagon to either union or confederate for heavy reputation boost.

New Orleans: Noah NPC
+20 confederate if you call the city guards as he is a slave on the run
+? to union if you deliver Noah to his destion which is a union city

Richmond: Lewish NPC
+15 confederate if you deliver Lewish to a confederate hospital, it is a weird bug that it is random so it might ask you to deliver him to Memphis once it is already captured by union, but it will still give you confederate reputation
+? to union if you bring him to union custory

Indianapolis: Lincoln
+20 to union if you bring Abraham Lincoln to Washington before the quest time expires.

There are a few more, but not much more, perhaps 1-2 more but i not wrote up all, please share the missed ones while you playing the game, thanks.

Double kill
Kill 2 foes with one blast.

Triple Kill
Kill 3 foes with one blast.

This is actually quite simple. Use your TNT to kill 3 enemies at the same time, but i believe it not working properly as i killed only 2 enemy + 1 passanger with the same blast the Triple Kill unlocked, so i believe it is exploitable with passangers or perhaps even with crew members.

Sheriff
Kill 500 foes.

You can get it in multiple games so it will come eventually.

Daredevil
Break land speed record - reach 75 miles per hour!

Yes, you thinking right now that this isn't a combat achievement. You is wrong. As traveling with this or higher speed on the map not unlocks the achievement, you need to reach this speek on a combat map while trying to escape enemies.

Family Embraces
Locate all members of your kin and help them out.

Just do the main quests during the campaign and you should have it but i believe this is missable as you need to cure your sister which is a timed quest, you probably can't get this achievement if you fail that one.

Victory for Family Honor!
Collect 51% shares and regain family ownership of the company.

This achievement is awarded for succesfully finishing the base game campaign.

Сurious person
Thank you for watching the credits at the end of the campaign :)

Yes, watching credits from main menu not count, so first you need finish the campaign then let the credits roll. Please keep in mind that if you own the West DLC there will be no credits after the base game campaign as game continues with the DLC story. This means that you need to get to the end of the DLC too which will end when you open your factory in Omaha.

Le Voyage dans la Lune
Ride 380 000 km on a single locomotive.

Have fun to repair your locomotive at every second station, this is very annoying quest. Yes, you need to it with one single locomitive:



Been Far and Wide
Cover 1 million miles during all sessions of the game.

A very pointless achievement as you wont be at more than 200-300k after finished main+base campaign. Suggested to do it casually while you watching some series so it wont be a real time waste. Sierra train is recommended, as that one is the fastest, i saved game and kept selecting the Portland-Omaha-Jacksonville path for a good ~1600, then back from Jacksonville-Omaha-Portland and the repeat. You can travel about 40k miles that way easily before the Sierra will have its first malfunction, no point to repair it (if you already donewith Le Voyage), just better and faster to reload the game where you have your Sierra with 0-1k mileage.