Walden, a game

You can do this achievement on the same playthrough you are using for the Hermit achievement. However, you must wait until after you have received the Hermit achievement to unlock this one as this requires you to go into Concord.

If you go to the General Store in Concord, and you go over to the household tab, you will see you have an option to pay back taxes. This costs $9. DO NOT CLICK THIS YET. When you pay this 9 dollars, you will unlock another achievement, but be LOCKED out of this one.

What I did was make a save first, payed the $9 (Taxpayer achievement), then reloaded the save and played as normal. By playing normally (not paying the $9) you will be thrown into jail at one point and get this achievement too.

Alternatively you can just wait until you get thrown into jail and then when you get out you can pay the taxes, but you will lose the $9.