No harm in confirming.

Well, that completely ignores the fact that you are potentially harming sellers when you put a house under contract and nobody wants it. 

He doesn't like to clean his house and smokes like a chimney but he's not leaving food around, he's not interfering with anyone, he's not damaging the property beyond the surface cosmetic damage that's already been done, and he's not harming himself.

Only being able to get sub-optimal financing will generally harm values more than what you "get" in value from the 5th unit.This is why you don't see a lot of 5-10ish unit properties.

Plus if it's not a rush then no harm in waiting for the right person to return.

She needs to take responsibility for her financial situation and you may be doing more harm than good by incentivizing bad habits. 

Digging in to public records and calling police, we found that tenant was arrested for "manufacturing controlled substance between 4g to 200g".Tenant was not trouble maker but here's the history:1.

No one else here will be harmed by whatever you decide; good or bad.Don't take the decision lightly, but also don't just listen to the negative comments either.

Live in flip can work here but I have seen many DIY "improvements" in Moreno Valley that harm the long term prospects for the home.

You need to make the stars and planets line up, and you better be in a position to take the property down if you cannot move it - otherwise you WILL be another wholesaler out there harming sellers.