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@Anthony BuccaneroHi Anthony,My wife and I are also located in the Twin Cities, and relatively new to real estate investing.

You might want to take a look at this relatively recent discussion thread for some counter arguments to what one might think of as the "sale pitch:"https://www.biggerpockets.com/...

This seems relatively unethical.

It was relatively straightforward.

It may be that to qualify for an ADU, the occupant may have to be a relative.

For the HOA boards that I am on, all communication related to a payment plan would have come through the management company as drafted and handled by their attorney on behalf of the HOA.A payment plan that was discussed in writing (email), drafted and signed by you (thus agreed to), and then has been acted upon as agreed by all parties for 7 months (they accepted the payments) - IMHO is effectively "executed".

however I feel he would try to find roommate or something, since there is nothing mentioned related to it in lease , can I just deny saying sublease / roommates are not allowed.

If you have good or bad success stories related to out of state investing, I would definitely like to discuss those. 

Of course it also all related to time value of money, a concept in which the general public is quite weak on comprehending.