You know how a snowball gets bigger and bigger the more your roll it? 

Any well-run NOO STR close to the nightlife/universities/sporting events does well, along with medium-term rentals for travel nurses, people giving Nashville a "test run", etc.

But at that price point , that will be fairly minor.Once you hold the hard money loans for the seasoning period the portfolio lender requires, just roll over into that.

Those Annuities don't sound great, 6.4% yield if just you on the policy and only 5.8% if you add your wife to inherit the policy if you die someday (sorry but high likelihood, nothing lasts forever)consider as recc above, find a few good syndicators with several upcoming deals you can identify within 45 days of the sale of your condos (sell all 15 as a package to some investor), then invest as a TIC, tenant in common, with one syndication deal, there won't be any fees, then make sure it's a longer term 10 year at least investment, then keep rolling until death.

House hacking is one of the most risk-averse residential investment strategies and will allow you to test the waters and strategically plan from there. 

Also, I was able to roll fees into the loan amount.

Perhaps a tool like this could help spot supply-demand imbalances and/or misspriced lots; then those under-$40k lots (avg) could be bought & resold for 1.3-1.5x.Here's a public test of the currently listed lots, three per state, suggested by the tool:GA:- https://www.realtor.com/realestateandhomes-detail/Ralston-Ga...- https://www.realtor.com/realestateandhomes-detail/71-Laurel-...- https://www.realtor.com/realestateandhomes-detail/Aubery-Ln-...ME:- https://www.realtor.com/realestateandhomes-detail/68-Quarry-...- https://www.realtor.com/realestateandhomes-detail/9-Surry-By...- https://www.realtor.com/realestateandhomes-detail/Sunset-Hil...NC:- https://www.realtor.com/realestateandhomes-detail/Old-Crows-...- https://www.realtor.com/realestateandhomes-detail/Turkey-Run...- https://www.realtor.com/realestateandhomes-detail/Bear-Cliff...NY:- https://www.realtor.com/realestateandhomes-detail/Hemlock-Ln...- https://www.realtor.com/realestateandhomes-detail/Middlefiel...- https://www.realtor.com/realestateandhomes-detail/231-Burke-...PA:- https://www.realtor.com/realestateandhomes-detail/Purple-Mar...- https://www.realtor.com/realestateandhomes-detail/14-Pocono-...- https://www.realtor.com/realestateandhomes-detail/Billy-Ln-L...VA:- https://www.realtor.com/realestateandhomes-detail/Dillards-H...- https://www.realtor.com/realestateandhomes-detail/Egypt-Bend...- https://www.realtor.com/realestateandhomes-detail/Riverbend-...The areas where the tool "looks" were pre-screened.

We never took out the equity from the property; however, if I were to do it again, I would likely have done a cash-out refinance or a HELOC so you can pull out the equity and roll it into the next deal.

However, they bring time-tested methods and valuable experience to the table.Younger Investors: They’re often viewed as energetic, motivated, and quick to embrace new technology.

You get the benefit of 2 years+ of appreciation, tax free gains, protect yourself from buying in a crappy neighborhood because it looks good on paper - you're going to live there...the best test for a good investment location is if it is a desirable place to live - and your risk of running out of cash is lower because you can take your time.