It seems I could easily sell it for a good price, but it might be hard to find a good deal on a suitable replacement...

It's more common because there's a lot of houses in Tampa that are <800sf 2 bedrooms / 1 bathrooms and that's not suitable to families anymore.

The color scheme of the house isn't my style and the house might be over priced for the immediate area.The answer is always lower the price.

Here's what you need to know (this was taken directly from the Fannie Mae selling guide):The basic "Second Home" Requirements are:must be occupied by the borrower for some portion of the yearis restricted to one-unit dwellingsmust be suitable for year-round occupancythe borrower must have exclusive control over the propertymust not be rental property or a timeshare arrangementcannot be subject to any agreements that give a management firm control over the occupancy of the property***If the lender identifies rental income from the property, the loan is eligible for delivery as a second home as long as the income is not used for qualifying purposes, and all other requirements for second homes are met (including the occupancy requirement above).So as long as you can fit the second home into those points above, you can acquire financing for a 2nd home.HOWEVER (and this is a big however) there are these things called OVERLAYS. 

These are the old-style radiators, if that helps.

We plan to purchase a house BRRRR style and ideally keep the momentum going with several purchases to follow. 

While this style may be ideal have you been able to find anything that fits this criteria?

I use propertyware but that is more property management style operations.

A little background...the property was built in 1972, 2 story garden style that are comprised of 12 two's and 8 ones.

Even if there was an Amazon style website with an "add to cart" feature the same recording paperwork and title paperwork would still apply