One thing I'd like to do going forward is optimize my leasing so they don't expire between the months of November-March.

It allows them to keep those afloat and can collect fees on that side by retaining ownership of the deal. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Sometimes maybe often times they aren't doing enough to track down the owner or owner's heirs and just collecting checks from the court.

Second, you left out the fact that owners who don't/didn't clean up -- in Florida or elsewhere -- had their land cleaned up by the government (local ones too) and then the land was seized or liened if the owners/insurers dragged their collective feet.

Build 2 or 3, get them running, collect some cash-flow, and see how the business goes.

1) I always use zillow to list new properties and use there platform to accept zillow applications2) Doorloop for management that includes accounting, repository for documents like leases, collect rents, tenant communications3) Received lease agreement from a lawyer

If you don't want the property any more a 1031 is probably your best bet, unless it's got a huge capital gains capture in which case you could just take your tax lumps and collect your funds. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

So should your facilitator.4) As a trustee, you can now write a check or wire money into any investment that follows retirement plan rules (no artwork, collectibles, alcohol, insurance, etc., and no disqualified parties).