I have seen retail centers for instance where if it is turned sideways or building is situated behind another retail center then harder to rent and rents drop to fill it with lease up.How good is the cross traffic from other sites to this tenant box space?

In this situation, should the seller be responsible for the sewage pipe repair cost?

3-this is our first rental so what am I missing in this situation?

Mortgage for situation 1 would be around 2,500/mo. 

Confront the situation? 

If so.... instead of buying the multi family for $100K..... see if you and the seller can come to an agreement where you buy the multi family for $150k on the premise that they will Warranty Deed (literally just sign over) the house to you.That’s what I did in Cleveland earlier this year with literally the same type of situation.

Would this be beneficial for the family regarding estate taxes (FIL is in very good health and not foreseen to have many health issues in the next decide)We welcome your thoughts and ideas on how we can make the most of this situation and arrangement.

Have you ever gotten a hardship variance in this kind of situation?

If you did get into a situation where it was a failed exchange maybe look at Opportunity Zones as another option?

Roommate situations can be tough enough for a landlord as it is so adding a bad tenant on top of that is not a good idea.