As a small business owner in a previous life, I found the bookkeeping super daunting, despite my love for numbers, budgets, & just data in general! 

Rents are either stabilizing or lowering in Florida, in general.

People are generally pretty active there.

General advice: use a knowledgeable independent agent. 

How many properties will you purchase in the next 1-3 years and generally what will they be worth?

This is generally when depreciation pushes an otherwise positive profit to zero or below. 

Lastly, unless you're married to this particular property, you should keep an eye out for other properties that just might be as sweet a deal.Also, about the HELOC, once it’s funded, those funds can generally be used for any purpose but double check with your lender JIC.

Below is a general description of the properties they are willing and able to rent:Type: Single-familyConfiguration: 3+ bedrooms, 2+ baths, 2+ car garages, 1,100 to 2,500 SF, one or two stories, lot size 3,000 SF to 7,000 SF.Rent range: $1,900/Mo to $2,400/MoLocation: See the map below for the general areasToday, these properties cost between $350,000 and $475,000.

And in general, do you believe it is worth the 25k+ price tag?

Condo's are generally bad investments, and unless you feel like tax "savings" are the saving grace for it I would step away.