@Nick Colamarino - We aren't Tampa either but have some unique visiting opportunities.

Most lenders require that a combination of the guaranty entitlement and any cash down payment must equal at least 25 percent of the reasonable value or sales price of the property, whichever is less.

For 2 people taking out a mortgage together it's increased to 5 times your combined earnings.

But I now have a unique situation and would like to get some feedback (from people outside of my non-real estate investing family and friends).  

Either I can start to manage them all full time and start a small property management company and quit my job, or re-leverage after paying them off to diversify into commercial properties (hotels, apartments, etc)I figure 20 properties at $500 =$10kAfter paying off mortgages cashflow should be $20kThat's $240,000 a year which is more than me and my brother make combined now.I am most concerned with cashflow and purchase price of the property.

There are tons of unique things about the property, but without listing everything, what are some creative financial solutions we can do for me to take over the house?

It's great area with combination of older communities and new communities like Riverstone, Telfair, Sienna etc., As @Louis Craig mentioned it's all higher price point. 

You have to either buy cheaper houses that you can easily afford, or make sure that you have enough cash in the bank to cover any vacancies and large repairs.Or be very tedious about your property management and make sure you can replace the tenants quickly which is a combination of understanding your market, pricing, etc.

Many MB and NMB banks don't finance fractured condos (the are Fannie Mae 'non-conforming') and those that do will look at combined value limits. for instance, 1st and 2nd mortgages (including a LOC if you can find one on NOO) will be 70% on a FNMA N-C fractured condo: 80K * 70% = 56K.

Most lenders want your combined loan  balance (primary loan, secondary loan... plus HELOC) to be 85% or less.Right now, you're already sitting at 80%-85%+ depending how long you've owned the home and how much it will appraise for.