I think the biggest block to getting anything like this accepted is building codes. 

It also seemed like I was working for the banks, as that was my biggest expense every month. 

For now I am looking in the broader Miami area, since I would preferably house hack a duplex and need to be somewhat close to my main work.As for questions I think the biggest unknown right now for me mostly revolves around the timeline and order of steps.

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From 6 years of being in real estate, I’m far from an expert, but the three regrets I hear the most are:1) I wish I started sooner2) I wish I bought more3) I wish I never soldMy takeaways from these ...

Our biggest challenge in the beginning was our on-site manager.

Laud area-Cash flow is minimal, $300 a month-Selling now would allow opening up of equity to redeploy in another market with over 2x the cash flow for a new build-New market won't appreciate as much as FL though (not even close)-Current home will likely get hit with higher taxes, insurance etc. in coming year and years to come-Biggest reason to consider just keeping current property?

I would look into them and try to figure out what their biggest roadblocks were.

In anything, people are always the biggest variable, so it can happen to anyone, but adding in a variable of someone you don't really know exasperates that risk.If you just want "boots on the ground," hire a local property management company, and don't go with the cheapest option.

So I haven't officially started yet as we're out of state, but I'm thinking after I start driving for dollars and building a list to market to, the next biggest hurdle will be a buyer list, but from what I've been told, the right deal will draw the money.