Paint has become quite expensive and costs can certainly run that high. 

He was previously my teacher in high school, so I've had a relationship with him and I've signed a buyer's agreement with him.

"Could this be a time to pickup a decent property for a bit of a steal there (at least relative to how crazy high the market has been recently)"Yes exactly

True mate,Always needed to get eyes on the property.Even if it meant sticking my nose on every window and looking through.Even the basement windows lolI think it's too high risk buying completely blind and not doing at least that.Ideal world, the back door is unlocked.And luckily for me "It was always unlocked" by me hahahaha Lol, yeah, I gotcha.

Hey Paul, I would highly reconsider doing rent by the room.

Banks often have very rigid requirements, such as high credit scores and a detailed financial history as well as lots of paperwork.Private Money Lenders: Faster and more flexible.

This year, when I listed it for sale, it got multiple offers, and we set a new record high price of $705,000 for ~800 sf.

A HELOC may be an option but I'm full time real estate (no W2) and have a couple properties and my DTI is relatively high. 

And I generally require a sponsor that has full real estate cycle experience with little to no money lost, low leverage, high skin in the game and reasonable fees and promotes.However, other investors will look at these deals as bad/too boring for them because they are more aggressive and not concerned about the risks of default, refinance, interest rates changing etc.

Taxes are high too, with new assessments soon (but still lower than Cuyahoga Cty).