For this achievement you need to sell to Jack Tarinton
This is how I got the achievement, worked first try.
Credit to Ted Turner III on steam - https://steamcommunity.com/sharedfiles/filedetails/?id=14219...
His guide reads as follows
How to sell to Jack Tarinton.....
--- If you forget a window, cockroach, bed or radiator, and the achievement will not unlock for you, then it is not my fault and you should read and understand the guide again ---
1. Buy Variable Woman's House.
2. Clean outside of house first. Make sure every window is clean and the house is completely cleaned inside and out and all radiators are mounted! Kill all Cockroaches!
3. First room on right sell shelves and clean windows
4. Sell everything in the Kitchen, even the counters. there should be nothing in there at all
5. Sell everything in living room exept coffee table and leave coffee table were it is
6. 1st Bedroom on left sell everything
7. Bathroom on right sell sink and toilet and heating radiator, roaches are hiding behind radiator.
Then buy sink 47.40 and toilet 53.29 and replace radiator
8. In Master bedroom sell the 2 shelves, then in closet sell the shelves
9. Master bathroom sell shower and sink and buy new shower and moutable sink 47.40
10. In master bedroom buy single bed Mantis 100.70 and that's all for master bedroom
11. There are 2 more bed rooms.....make sure that you sell all furniture in both bedrooms, then the bedroom at the end of the hall the gray one buy Single bed Mantis 100.70 and that is all, so in master bedroom and the gray bedroom at the end of the hall all you should have is 1 single bed Mantis 100.70
12. In living Room buy Couch Archaic 139.97 and put under window in front of coffee table that you left there. then for TV buy Monitor 109.39 and place on coffee table facing couch. Now this is important, buy Refrigerator Mono 196.07 then place to left of couch in corner in living room.
--- And do not sell any other things like a bathtub, it will not work if you sell too much ---