In my opinion, accounting is not that difficult, but saving all these receipts digitally could be quite a hassle.At the end of the tax year, your tax guy will ask you to provide each rental with schedule E.

Rob,I can totally dig it. 

Your family (kids schools, friends, your friends, etc) should all come into play in your decision as well so if staying is "best for personal life for you and fam, then pick that and use your other options to see where and how to invest.Here are a few options to consider along with what you have already named: Investing in a syndication with your savings, cash out refi, or any other liquid funds you have can be a goo place to earn double digit annual returns and get economies of scale with your investments.

I selected a specific area in Houston, bought a crap house for $75K when EVERYONE told me it was a bad deal and my interest was double digits (which sucked but I didn't plan at all and my only option was owner financing), did as much of the Reno I could myself (around $25K or so, stopped at HVAC, roof, foundation, etc) rented it out for 5 years, made over $100K doing so, and then I was ready to put another $60K into it to quadruple the purchase price but my health deteriorated and I sold it (for double what I paid).  

Personally I would recommend sticking with free or mostly free strategies when starting out, as it will take you time to learn the business, the objections/situations you will face from potential clients, and so much more.

Steven Pinker (a well known and highly respected cognitive psychologist) talks and writes about how--by many objective measures--life is much better for most people today than in previous generations.

All real-world assets in the very near future will be digitized and investable via nft's and tokenization. 

I have yet to come across a post on this forum that involves a bad tenant, who had a good credit score.I’m sure it’s not perfect, but credit score seems to be the closest thing we have as landlords to assurance that the tenant won’t cause problems and will pay on time.All the issues you discuss with debt - these are showing up on the scoreboard (his credit score).It’s simple, objective, and fair.

.- I have lots of digital color photos showing the damages.

Just underwrite the deal based on your objective and risk tolerance.