I would recommend you really take your time selecting the right software.

Has anyone ever experienced this sort of situation?

Use some for buy and hold (I personally would prefer apartments rather than buying a few single family homes) and some for lending/trust deed investing.In either category, you must know what you are doing, know how to vet the investment, how to vet the sponsor (if investing in a larger fund of some sort), the laws and regulations on the lending side, how to investigate which areas to invest in buy and hold and notes/trust deeds for that matter.So as you have already said several times, lots to think about . . . 

I help all sorts of investors from all over and those in KC find replacement properties.

That easy question to answer will be a really great litmus test in your due diligence toolbox.If you are evaluating a REIT, it would be wise and prudent to do your homework and select the appropriate professional to guide you.

AS we did this for a few decades in a few select counties you would see the same names and same parcels pop up only to be redeemed last minute as you note..

Digitize physical receipts for easy storage and use a consistent naming convention for easy sorting - 2024.03.25 Home Depot. 3.

They charge $1000 if you buy one of their pre selected properties.

You sort of noted in your opening comment: a track record IN REAL ESTATE, should be measured in decades, not years.  

In most cases, the contingent fee option is selected because litigation is expensive and most plaintiff's cannot front the costs.