The rental is in Tampa Heights and around the $900-1,000/Mo range.Do those investing in areas prone to hurricanes invest in impact windows or storm shutters?

In this current rental market, you may have positive cash flow.With the numbers you posted, to flip it looks like you're coming out with possible ROI. 

I'm positive you will find a funding source there. 

Assuming similar numbers provided in Option 1 and 2, as well as 3% appreciation for the year; rental income would be positive $2500 for the year, equity of $130k (assuming $0 downpayment and considering remodel costs), all closing costs of $45k, and your rent of $26,500.  

I ran a stress test at a 10% drop in rents and it was still positive cash flow (barely). 

Saving 50% or more of each paycheck will help put you in a position of financial strength so you can wholesale or buy your first property or anything else for that matter.

If your portfolio is a good deal you won't have an issue finding buyers.If you truly have control of a package is one thing, if you are trying to play match maker with no real control, that is a weaker position.

I am not sure of my timeline but I'm gonna set a goal of positive cash flow within the next 12 months. 

Sure, you could argue that you'd be collecting rent from your tenants, but good luck finding a multi that has enough positive cash flow to cover the entire mortgage, taxes, insurance, vacancy, maintenance, capex and your living expenses, food, gas, utilities, etc.

Does anyone have specific advice on how to proceed (aside from I should not have put myself in this position?)