I learned the hard way how to shut off water and how to winterize.

Many people have a mortgage on a property where the land value is much greater than the home (aka near the water) and insurance is not able to pay off your entire outstanding mortgage.

Compare other rentals with a similar size, location and bedroom count to get an estimate of what the rent would be while you're living there.

its cheap  compared to what you get I found a strict foreclosure in Oregon that their site was on the only one tracking it and we made over 300k on that one deal. 

Granted this was on plots of land I didn't pay for, and that are already connected to the city's water and sewer, so there's a lot of savings there, but I'm hoping if it turns out to be this good of a deal I can still scoop up land and keep going

In one of the 3 fundamental human needs (food, water, shelter).

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

In addition, condos tend to not appreciate as fast in value compared to single-family or multi-family homes. 

I a factoring in the replacement of the AC unit and potentially the water heater, and the cosmetic thins (I would do myself) to get it to rentable standard.

If it's a long-term play, the potential savings on PMI with a conventional loan could be significant.Have you compared rates for both options?