Even if everything goes great on your C class investment, the cash flow generated is normally not enough to make you rich.   

With all the horror stories about fake sales of people’s properties and AI generated documents, you wouldn’t think there would be a demand for this.I found this one but no idea if it’s legitimatehttps://www.propertyfraudalert.com/FLHillsborough

This seems pretty random.

If you can keep your home data up to date and make the site user friendly your already off to a good start.Just do not become a lead generating platform when you do that you end up with a higher percentage of users who fail to return. 

We (I work at Azibo, just a disclaimer) have quite robust accounting capabilities and time saving features like Schedule E generation and automated  transaction tagging rules.

I’m ok waiting 5-10 years to build generational wealth off my LTRs.

I didn't phase that correctly and should have put an emphasis on "Traditional Sale".I am willing to sell but want to do it "creatively" - if you will - to generate funds and positive cash flow from the note I would hold against the property.

The problem is that it seems that it will be very difficult to generate even a neutral cash flow given the high HOA fees, taxes, and insurance in Florida.

I am assuming if the property generates income it would be better in her name.

If you're more conservative, you might want to increase your fixed income allocation.Income needs: If you plan to live off your investments in retirement, ensure your portfolio generates sufficient income to cover your expenses.Remember, this is a general guideline.