I have family in construction who have looked at it and feel it has fairly solid bones and I like the location and think it's on the way up.

This is literally what a pre-approval letter from a lender does - it shows that a lender has taken a solid look at the buyer and confirmed that there is a decent probability that they will get the loan needed to close.

Your strategy sounds solid on paper, but moving extremely fast with lots of moving parts and a lot of debt. 

For example, a few years back, I was working with an investor who wanted to break into the Phoenix market - a solid choice, by the way, because of the rental yields—and we ended up uncovering an off-market duplex that wasn't even on her radar.

Democracy, solid demographics, well educated, diversified economy.

With this being a high rent home and them being solid tenants, that is something we must keep in mind (but also not allow us to act foolishly in the name of retention).

I remember about 6 otr 7 years ago flying into Chicago to check on my deals there and lake Michigan was Frozen solid  I had never seen that before.

Trusting lenders, agents, and contractors can be tough, but building a solid team and doing your due diligence will help ease that process.

Tampa’s a prime spot right now, and starting with fix-and-flips is a solid choice for building capital.

Bottom line is you have to have a solid grip on what properties rent for in your market - not only direct comps to what you have but also what's above and below you, because tenants can and will move based on affordability both ways ("downsizing" to save money or "upsizing" because an extra $50/100 gets them a much nicer place).Once you intimately know what your market is, and what's available, you can compare what you are charging to those figures and adjust accordingly.