Just be careful to offer all acceptable applicants the same options to avoid Fair Housing issues and DOCUMENT everything!

If you do a 1031 exchange you can avoid paying capital gains. 

He also lived in Property A for ~2 years within the last 5 years (though he's been told by his CPA that he likely won't be able to avoid *any* capital gains because of the way his previous returns were filed.

Seller's with multiple offers may want to avoid making repairs wherever possible.- writing a personal letter to the seller highlighting your personal story, interest in the property, love of the neighborhood, etc... to my knowledge, this has not been proven to be effective.Best of luck to you on the offer!

Can you avoid that tax in 2021 since you will not have lived in the state at all? 

Or who I should avoid.

My advise is should you take this leap, try your best to avoid your tenants discovering you're the owner.

Would be easy to add your husband and then you'll have additional income and the debt issue probably goes away but obviously if he wants nothing to do with it then you could just not involve him :)  Depending on how you file taxes, it may still show up on the tax returns - so he may not be able to fully avoid being associated with it. 

This means avoid going into the trenches (why and how) of topics during the meeting .

I would avoid the risk also and especially since multi units do not require the SD.