The vacation side is more of a business and requires a lot more work but the affordable housing side is less labor intensive. 

That 2nd requirement is  what makes it close to basically impossible with a W2 job.

Hey Deirdre,To address your questions:Providing freedom by handling day-to-day operations.Offering peace of mind through proactive maintenance and tenant communication.Reducing risks by staying ahead of legal requirements, tenant screening, and dispute resolution.Enhancing the bottom line by identifying cost-saving opportunities while ensuring tenant satisfaction to reduce turnover.Is the experience still important when the property thrives financially?

The seller requires a cash purchase & I’m exploring creative ways to structure the deal.

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

The only reason I got an LLC was to buy a commercial property because it was a requirement of the lender.

The PM business is not an easy business and most have fair fees for the work that's required.  

Credit is a factor as bad credit may limit options, or may have the lender require you to put 10 or 20 years of taxes and insurance into escrow. 

Maybe you could extend the closings with some additional earnest money (even if you release it) and buy the time so you can simply do a regular 1031 exchange.  

You simply get a discount on this purchase, equal to your tax rate/bracket.