FWIW and in case you can glean any ideas from it:
We built our net worth through properties over 30+ years, to enable us to retire, not being entitled to any form of pensions! Bought building lots, built and sold, renovation business and bought revenues to rent out etc etc. We sold our last revenue in May 2005 (had enough dealing with vacancies whilst trying to find the "right" tenants, and then the "hard luck" stories and lack of respect how they treated our properties). Then in Apr 2006 our market was going ballistic, so we ordered a condo to be built for eldest daughter to live in and pay reduced rent than market rate = worse thing we ever did, as took two years to deliver in July 2008, by which time she was onto different things and the wheels had fallen off the economic bus so to speak = negative equity. Finally sold it this August 15th, after being 9 months on the market for $50K less than we paid for it (ouch, can you feel we're hurting after a decade of ownership!). Anyway, long story short the times and real estate market places are a changing, and we too have seen how little attention property managers place on looking after others rental units for the most part - think of them operating on a "numbers game". If we can't be hands on ourselves to manage it, and in more confident economic times whilst doing so we are so glad and relieved to have now sold the last two this year. There's a lot to be said about peace of mind at times over money we've ascertained, especially as we've got older, more cynical and burnt a few too many times. Believe me for us the relief versus the tax bill we had to pay was worth it. Feels great right now.
We are trying to sell our last property (going on the market 17th Oct) in Fla, and then for a little higher return than we'd get in the banks, we're going to carry interest only, on our main acreage for our youngest daughter and her soon to be husband. They are going to save the difference they'd be paying down on a mortgage as principal and then as and when they are comfortable they can at any juncture apply for their own mortgage and buy it outright from us at the price as if we'd sold it to them today. Really doesn't matter, as when we get called to the old pearly gates she'd get it all anyway. In the meantime the money they pay us as interest (more favourable than bank deals) gives us more than if we'd put it in the bank on a full sale basis, and they get a better deal than through the banks financing commitments etc. WIN-WIN.
The rest of our savings/accounts we are putting into a self directed "Couch Potato" set up, with a goal of returning at least a 4% return ideally but average 5 & 10 year returns has been showing much much higher than that including considering real lower returns the past couple of years. So ........ there's never any guarantees on anything in life, but we are seriously of the mindset after getting over the disappointment on low interest rate returns, that "peace of mind" being debt free, and property maintenance/billing free is priceless.
Good luck Joel on whatever you decide moving forwards.
FTW.
It Takes No More Effort To Aim High Than To Aim Low - Reach For The Stars