Though North St Petersburg may be just as easy to get to MacDill.Regarding rental properties I dislike HOAs dictacting your profit margin with escalating fees and assessments.

I guess I could dislike anything in that scenario 

Call 5 ask them what parts of the city they like/dislike and why.

If people ask let them know you're new to real estate, but focus on seeing what their problems are or where they are having bottlenecks in their process and offer to help them do the things they dislike or struggle at.

If you dislike their art chances are you won't like their renovations.

Last thing first - - never understood why so many dislike commercial financing, as it operates to ensure you get a cash flow - - that's what the DSCR indicates. 

If one doesn't take action, all this is just academics, and you have no idea how much I dislike academics.That being said...

As for finding a good agent, I would make a list of your needs, likes and dis-likes, then start interviewing.

Its just that they dislike losing it more.

Now, if you had a total PV of $10M, and all the properties involved had Positive CF, what could/should that new CF be.Although you may not like debt, that dislike is what's holding you back from that magical $15k/month CF you want.