If I get the situation correctly, youre wanting to exit retirement and pull cash out of your home to use to flip a property in FL to generate income to live off of.

During this time you are not generating any return from the money invested in the ADU.

It'll be up to the next generation to figure out if they want to build an empire or not. 

I subscribe to PropStream and Flipster and was wondering if either of these sites you use or you prefer a different program to find distressed properties and generate lead lists?

However, I made the error early in my career of thinking I was generating way more cash than I thought I was. 

regarding roofs  pray for hail storms and then replace .. in those type assets that are really priced for cash flow.. values will rise only when rents rise.. as non of them will ever go owner occ.. at least that is generally what happens with this type of housing.. the value play is the tenant pays off your home and your home generates enough cash flow to break even at best and feed it a little bit over time.. then at the end of your mortgage term 30 years you now have say 2 mil of paid for assets the real money is made on these assets cash flow wise ONLY if you pay cash IMHO

Still trying to get through some sales to generate cash.

There is life stages to investing, and the math is clear that strategic debt use, strategic leverage, pyramiding, appreciation, is the wealth generator. 

Many of my customers who are traveling nurses buy condos or townhomes in Florida as vacation homes, then rent them out when they're not in town.This system has proven to be very lucrative, as it allows them to service the mortgage debt and generate a good cash flow.

The frameworks others have presented of viewing the site as a lead-generation tool where you, as the host, are handling all the payment processing and screening is pretty accurate.