I still don't know enough but I'm a learner (and usually a quick one) and I see me joining this amazing community as the first 'taking action' step.I put myself a short-term goal of becoming a long-distance owner of my first USA rental / flipping / wholesaling Real Estate property within the next 9 months.

Now, ALL of my out of town stuff (further than walking distance) has an experienced investor with it. 

Considering to do long distance BRRRR (my first investment) in Florida but what a good location/market to start? 

Look for a small town with major employers within commuting distance, and pick the one with the best school systems.

Personally, I have seen too much stuff and I would not invest within walking distance to any of the blue areas.As long as I have been buying properties, over 10 years now, the bad areas have not changed much, so I have little hope that they will turn all the sudden.

What kind of land rental can you do from long distance? 

From your post, clearly you have surmised that the NYC area and $20K isn't going to cut it, but don't limit yourself to geographic constraints, you can find opportunities across the country to make that initial amount work.

I enjoy surfing and love living walking distance to the ocean. 

It is walking distance to an elementary, middle and high school.

I have to agree I feel I'm at my best performance when I'm somewhat at a distance.