I want to learn RE investing, but I just don't know if I'm smart enough to do it. 

I've shopped around, and while nothing's pretty, there are a few viable prices for private flood insurance companies.

One exception to your thought process many times in those areas that decay like that Commercial LEAVES and the nice NEW shopping gets built where there are nice new homes and incomes that can afford to shop.. what a lot of these areas is left with is the corner liquor store .. you know the ones that have Bullitt proof windows and sell cigarettes' one at a time.. 

I know you said "worst case scenario" but it's smart to run the numbers conservatively.

.$490K * 80% LTV = $392K, less $225K payoff of old loans = $167,000 to go shopping for your first MF property. 

Le Marbella Tower Condominium is walking distance to the Atlantic Ocean, Samson Oceanfront Park, Sunny Isles Fishing Pier, Norman S.Edelman K-8, one of the best public schools in Miami-Dade County, shopping centers, and restaurants.

Smart thermostat or programmable is always a good idea for energy savings (more important if you are including utilities).

The property will cash flow around $275/month because of the lower mortgage payment (again, conservative estimate)I've had a ton of friends use the VA load with nothing down on primary residences turned rental properties and it seems like a good way to preserve capital - seems smart especially if I'm gonna be purchasing additional homes in the next year that may need $20,000+ in renovations.

I am concerned about cost to a degree but I feel if I have the correct guidance on what would be the smart way to use my money on the house it could be of huge value to me.Any and all suggestions and guidance are welcome and appreciated. 

As the others have stated as well your pricing seems high so shop it.