Plus, you'll have to see if there were any fees the brokerage house charged you that can be used to reduce the capital gains from the trading profits.As others who respond here will probably say, you should contact a good CPA who is very familiar with day traders and home office business expense.

Also you may wish to check out local investor groups such as Black Diamond REI in southern Mass and RIREIG in Rhode Island.Since you just bought your first property, I would recommend taking at least 6 months, 12 would be better, learning how to be a landlord of your first rental unit before acquiring another one.Learn about renting a unit out, tenant screening, collecting rent, repairs, capital improvements, handling moveouts, etc.

Also, that would be some friend to do all that for you.Is there not a way to handle this in normal divorce proceedings like force a liquidation of the property and pay her half, or pay her half to keep the property, or have her pay you half and you walk.Lots of other viable options here.... 

I've tried several ways of handling this, but the most successful strategy I've found is to have the tenants submit a paint swatch, and once you've approved it, you can hire painters (or paint yourself) to paint it that color, while charging the tenants for time + material.

How would you more seasoned landlords handle this situation?

Or someone would need to negotiate with the lien holders to get a reduced payoff.If you want to offer the deal here you will need to post in the Marketplace.

He doesn't have unlimited money but he is willing to fund pretty much as many deals as I can handle at a time.

I would say you handled this extremely fair, if not a bit too generous.

In your opinion, how should this matter be handled?

Then if you want to slough the numbers with a justification of how house hacking reduces your monthly mortgage/rent, at least you're armed with the analysis for both scenarios, and can make a qualified decision.Roughly, $500k purchase with $4000 monthly gross rents doesn't hit the 1% rule of monthly gross rents being 1% of the purchase price.