After a few years he'll lose the emotional attachment to the properties since he'll only have been getting payments for mortgage and you might be able to discount the note at that time.  

Until you meet outside Lender's seasoning requirements, couldn't you be your own bank?

The helix is not “assumable” in the true sense, as in they apply to your bank and become responsible for the loan And relieving you of the loan.  

Assuming the lender is unwilling to transfer the deed, or has a penalty attached to transferring deed. 

So you would be taking $70K - $75K+ to the bank.  

It would probably help if the story you told was about accessing the equity to purchase further income producing assets rather than fly to the caribbean and buy an Audi.By putting together a small but professional looking package and going to sit down with some community banks in person, I think you'll get a tremendous amount of experience and straight feedback on what's possible or not and why.Good luck!

PM is fine if you don't want global sharing.I've been using Airtable (which is excel like but let's me attach receipts to rows).  

Just ask yourself how much out of pocket is comfortable to you and just bank on 2 of the 4 wealth generators.

If I’m going the conventional loan route for a 4-plex out of state, do I need to find a lender in the area I’m investing or can my local banks lends for investment properties out of state?

I heard banks don't lend to LLCs so I'm a little confused on that.