I'd still get the house inspected.If you have this personal relationship with the flipper there should not be a reason you capture some equity at closing, even if it is nominal. 

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!

That way my investments are diversified between real estate and equities, and I capture the tax advantages of both the real estate and the retirement accounts. 

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.

The manufacturer of these models also sends two crew members to make connections, and all of the interior items and finishes are pre-installed, and stand tall against code.