I am not looking to provide monetary donations to other community programs, but would be willing to invest significantly in some sort of community outreach program of our own. 

I am hesitant to trust a third party airbnb manager over the long term, and even if you have a great management company, there are still a lot of items that are reliant on the ownership.  

You could end up with a non paying tenant or eviction and some major capex item simultaneously.

In NH at least, because of the sheer number of old multifamily building, even on the larger side, a lot of items are grandfathered in.  

There was no process in place for the removal of large items and none of the tenants thought to bring it to our attention!

I am looking to do my first two deals simultaneously (one 4-plex, one duplex, same town) and would like some advice on a few items.

I've always bought turnkeys and the only work I do on them is due diligence items.

@Ramsey Howard yes, two important items for what you are describing:1.

friend of mine is doing this in portlandia.. look at the big developments I think in the netherlands or other parts of Europe they are away ahead of usAlthough my buddy is more of a philanthropist with this particular endeavor he even donated a fully functional one to the collage... although he hopes to some day turn that around and make them viable financing for himself as well.. but i bet he has spent 250k or more on this so far.. all for science / construction lab at the collage

By purchasing the borrowers non-attached items we are able to give the borrower a small amount of money AFTER the closing while acting with integrity and within in the law.