Could you often or always get title to the property or you get money back from the debtor/ a third party who wins the auction sometimes? 

If you win this comparison, your partner loses.2.

Cash-flowing rentals in Florida right now are tough overall, so you won't pull up places for sale in the greater Orlando area, throw a dart at the metaphorical board, and find a property that easily cash flows.

Using a VA loan for a second property, where I’d move in and rent out my current home.When I made an offer on a fixer-upper (I didn’t win that bid), the loan officer mentioned it might be difficult to convince the underwriter why I’d need another VA loan for a second property in the same area, especially since the new home is almost identical to my current one (same size, age, school district, etc.).

I agree with wanting the first one to be a "win", I'm just concerned that makes it harder to find something that will cash flow.

You can easily find a turn-key property in the $250k range with cap rates around 6.

You will also have the ability to refinance the new purchase easily with a delayed purchase refinance (You can price these as a rate and term refinance), if you plan on only refinancing the purchase price + cost of improvements. 

At the auctions I attended the winning bid amounts varied from $80K-500K.  

However, I've found that www.netronline.com provides the same and is more easily accessed.Ted Thomas does everthing possible to keep students from interacting, so there is no Facebook or WhatsApp group established through the organization, but there may be groups established outside of the TT organization. 

There is no other service setup to almost solely win deal at the tax deed and foreclosure auctions.