With a dozen properties over 25 years I have yet to spend a dollar on a roof or painting a house exterior.

Deep cleaning, new paint, lots of cosmetic repairs.

It needs new carpet, everything needs to be painted, the bathtub needs to be reglazed, and some of the outlets are still 2-prong.

I have seen this in Milwaukee too many times, the only way to make it work is VERY hands-on.If you end up renting it in March for IDK net $200 the property will have lost a LOT more in the next 12 months just in condition vs what it looks like now (assuming that it is freshly painted?

Deep cleaning, new paint, lots of cosmetic repairs.

With fresh paint throughout inside and out, brand-new roof, dual HVAC systems, updated water heater, stainless steel appliances, lighting fixtures, outlets, countertops, and PEX plumbing just to name a few.

It seems that if you can find a good deal on the purchase price, are willing to do cosmetic updates (floors, painting, maybe a kitchen) you can get that 100-200/month cash flow.  

I would have talked to them BEFORE cancelling the painter and given them the option of which way to go, but since you already cancelled the painter I would simply charge them prorated rent for the 5 days until the painting is complete and deduct that from their deposit.

Painting, for instance- an amatuer could take their time and paint a house over the course of a couple weeks and do a great job, but a professional crew could do the entire job in a day. 

Assuming it’s not a 50 year old home with lead paint, asbestos, lead pipes, etc etc.