Most criminals defrauded the IRSI wonder what would happen if the people who combined lost like $2M all sent 1099's to him-I bet that would wake up the IRS but not sure if it would impact their claim later on.

I bet there are some ways you could proactively plan so the problem almost resolves itself. 

Reach out anytime

Also are you allowed to cash out at any time?

This would make it into two, two bedroom units with the intent of making them long term rentals.I'm guilty of having a lot of projects going at once so my focus right now is bringing the cottage to a point to refinance out of the private money and either make it our primary residence for a year for the financing perks or to go straight into a short term rental.With the four bedroom house I'm trying to decide if it's worth splitting into two units or if I should keep it a four bedroom rental.The cottage I'm also tempted to do mid term with to lower the turnover and maintenance but open to suggestions.The third property I'll probably just let the current renters pay the mortgage for the time being if I'm able to acquire it anytime soon.

I imagine you'll have the same issue with the unpermitted kitchenetteIf you can rent the property as a MTR then listing on Furnished Finder will probably be your best bet.

I think your thesis is sound in general, but I would want a hedge on my bet.

You can always sign a contract to buy the remaining properties anytime with a closing date scheduled for the future (not sure why he would want to do that though since we don't know what will happen appreciation-wise).

From what I'm reading here, and we immediately sought legal counsel on this, they're totally free to move out anytime they want.

Your best bet would be to hire a good property manager who screens well and knows what they're doing and you should be able to get good income over a few years.