I’m trying to familiarize myself with the area more thoroughly.it seems to have a stable increase in prices.Since I plan to live in the property initially, breaking even in the first year is my main goal. (5% down; PMI removed with renovation)However, I’m also wondering if it’s feasible to have some cash flow from such rentals, or if the risk of vacancy is high in this market.Any guidance or pointers from those experienced in this area would be greatly appreciated!

It makes sense for house mates, spouses etc. to be Additional Insured on a renter's Insurance policy if they also live there and keep their stuff there (although I think anyone on the lease is typically covered anyway).

I am currently living out of state so I have hired a property management company to handle this task, however, my home is still sitting vacant with very few prospective tenants.

Pace was the only one I encountered who showed up live, who is living these deals out every day and consistently finding ways to deliver (increasing) value to his community.

In the unlikely event that you are the exception that proves the rule, the rare 18 year old who can actually generate a serious income by wholesaling real estate, your day to day will look like the following: - You will door knock, cold call, send mailers, and otherwise create lists of people who are in the most desperate moments of their lives. 

I actually live Pinellas County.  

This has been my experience and I live in an ultra-competitive market.

A giant laundry room, a two-car garage, and a separate living room.

Especially if you built something to rent or live in. 

I used to live in Tokyo for 6 years and would like to find a reason to go back more regularly but let me know if you want to connect!