I envision this portfolio supporting me during my retirement years—though I still plan to work, just in a different capacity than I do today.I recently finished reading "How to Invest in Real Estate: The Ultimate Beginner's Guide" by Josh Dorkin and Brandon Turner, which has been incredibly helpful.

Creative ApproachesIf the organization is hesitant about a sale, consider proposing creative terms:Seller Financing: The non-profit could retain an income stream from the property by financing the purchase.Partnership or Lease-Purchase Agreement: Offer to lease the property with an option to buy, giving them time to evaluate the relationship.Donation or Support: Consider including a donation or offering support for their mission as part of the deal.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

This extra road frontage now also qualifies my property to be able to be legally converted into a triplex from a duplex.

The quotes were only a few hundred dollars extra annually.

I've allowed pets in my STR for five years and haven't had any problems except some extra cleaning a couple times, which was paid for by the guest. 

I've tried the lower 6-7% PMs and usually you'll either pay mark ups on repairs (what you've noted) or pay extra fees (i.e. labor hours, extra calls) that you may or may not notice. 

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I would have to get with the property manager and mimic the exact plans they have set up in the lease, all of which were probably customized by the PM to get a few extra dollars.  

Living in one unit and renting out the others could offset a significant portion of your mortgage, giving you extra breathing room as the sole income earner.