We have a potential buyer of a lot in St Augustine, FL who would like to build a new single family short term rental.

We are building a place with HELOCs then after it is built we will finance it and pay off our HELOC, at least thats our plan. 

You are off to a great start with your first one that cash flows. 

Quote from @Richa Wardhan: Hello everyone,For those who call St Augustine home/ investment home , how challenging is the process to build an ADU on your property in St Augustine?

I'm currently trying to build my list of interview questions that I would/could use when it comes to screening and finding the right Real Estate Agent.

I have a unique deal that the property owner is just wanting the builder to build him a home for "free" and he will sign over the land.

With a Condo, couple things to note:1) Financing can be a challenge, but as long as the building is in good condition, you should be fine.

Honestly, it seems like you’ve got more skin in the game than I do since I’m just getting started as a bird dog, but I really admire your approach.I think your focus on tax-efficient strategies and building a reliable team is spot on.

Engage an investor-focused realtor/broker in your preferred market (this is not a residential realtor) and start 'tire kicking' the market and properties that fit your criteria.

@Derick Jennings Without knowing more about your situation, I'd likely recommend a house hack, a strategy I wish I would have known about when I got started.