Most of them haven’t been maintained properly (think worst case scenario like bottles in vents, grease in plumbing, uneven floors , crawl space issues).

Quote from @Brian Kloft: I think a lot of the problems people have with failed inspections and such come from Landlords that don't like to maintain their properties.

Therefore, if your rental income doesn't keep up with inflation, you must consistently reduce your monthly expenses or return to work to compensate for decreased purchasing power to maintain your living standard.No matter how many properties you eventually own, unless rents outpace inflation, you can not achieve true financial freedom.Back to Your SituationYou stated, “I don't believe that the property will continue to appreciate or see the rent growth it has seen over the past few years.”

I’m concerned about having to maintain it.2.

An asphalt shingle roof often lasts 25 yrs, so you need to reserve $27/mo EVERY MONTH for 25 years to have $8k available in 25 yrs.  

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

I have a contemporaneous mileage log along w/ what was done each trip to go along with this.3) I am aware that for the IRS it is a red flag that I maintained a full time job over this period (a good amount of renovation work was done while working remotely waiting on jobs to finish).

I do not give my tenants the option to maintain the yard.

My goal is to build a portfolio to hold and maintain for the long-term.

Two potential challenges:1) Finding someone with ALL the necessary expertise2) Finding someone that has enough time or can work efficiently to maintain your list