I don't particularly want to sell my share of this property as it has appreciated quite a bit since we've initially invested and I'm hoping I can eventually get him moved out to turn it into a full-time rental property. 

If I proceed with this tenant, I'll post again to let everyone know how it turned out.

Mind you, we've got 3y left before the 4.5% ARM turns variable (+/-2% per year; min 2.5% / max 10.5%).3) ???

In turn, this makes me a big fan of HELCOs, but still, that initial investment is going to be a tough one.

Quote from @Minnina Smith: When you are just starting out with purchasing properties to turn into rentals.

It cost him another 3 months before he could start work turning the unit. 

Especially if you get a long term resident in the ADU and then you might can utilize them to help on your turns of the MTR. 

They're not bad kids, but they are kids. 4) CONSTANT TURNOVER80% of my properties turn over every single year.

Have sold several in the area breaking even turn key or 3-5% cash on cash return after renovation on first year.

Yes, turns out I do need an attorney in Dupage County if plaintiff is LLC ...