SPOILERS AHEAD.
WARNING: I consider this a rather boring way to complete the game, but it is an interesting thought exercise to try and play my own game in a way it was never intended to be played.
The objective is to play the game without performing any crimes or any sex acts/stripping, only tending bar at McCall's Bar. I also opted to do this without any of the bonus items from completed playthroughs, although quite a few of them would be helpful to the masochists who wish to attempt this.
Anyway, here is the general guide:
Start with the 'Coffee Cup' tattoo. Other tattoos that might help are the 'Rose Tattoo', 'Cat Palm', 'Coin Clock', or the 'Extra Food + Wetwipes' start.
Go to the Church to get 1 free food and the free wet wipes from Annabell.
Perform Russ' Day 1 quest of buying beer. Make sure to follow his entire story line as this will give you cash at the end of the day.
Have Mary come over at the End of Day 1 (6 free beers to drink to lower stress throughout the days).
Talk to Mary enough times that she gives you the tip jar (which will be allowed on the 2nd day)
At the end of Day 2 and 3, work for Russ to further his story line and earn some cash.
Have Russ fix your shower so you can stay with him, which will net you +1 energy per day.
Learn to drive the Futo NT-R (costs 3 energy and $70 total)
When the end of Day 6 comes around, work a shift at McCall's Bar
At Day 7, if you talk to Mary again, she'll offer you $100.
This is optional, but some random events can give you cash and reduce stress.
Your biggest enemy is going to be Stress. You'll want to make sure you have low Stress before ending the day on the early days so you don't lose any energy. Food is a somewhat neutral trade as you'll probably earn around $25 energy per bar shift. You might also want to keep some wet wipes handy, as you may need to wash up to improve your beauty.