@Mark F. is a local investor who I've had hours and hours of conversations and texts with, just talking shop.

It's a magnet for both tourists and business travelers.Brickell: A luxurious enclave known for attracting affluent visitors and business travelers.Midtown: A vibrant, upcoming area appealing to younger travelers seeking a mix of local culture, shopping, and dining.Given your budget and the goal of purchasing two condos, investing in a combination of these areas could optimize both appreciation and rental income.

The idea here is to pay off the principal of the $700,000 over the four period then when I get a loan for the remainder $550,000 it would be more affordable.

A couple of questions, although several have already been answered on this forum...Is it worth shopping around for multiple lenders due to perhaps differing terms on these (rates, restrictions, fees, etc) or are they all generally the same?

Similar with a SFH: I can at least get in the market with a 5% conventional loan not expecting cash flow but hoping appreciation will help me out in the next 2+ years and I will at least be able to put up the remainder of the expenses since I do live with my parents.I am young so I could be overthinking, but my end goal is to have a portfolio where I can cash flow enough within the next 5-15 years to let go of my job (5k clean a month).

So my other advice is keep your heloc at your primary bank or shop around till someone really wants your business 

Similar with a SFH: I can at least get in the market with a 5% conventional loan not expecting cash flow but hoping appreciation will help me out in the next 2+ years and I will at least be able to put up the remainder of the expenses since I do live with my parents.

Similar with a SFH: I can at least get in the market with a 5% conventional loan not expecting cash flow but hoping appreciation will help me out in the next 2+ years and I will at least be able to put up the remainder of the expenses since I do live with my parents. 

Finally- those closing costs seem pretty aggressive- maybe shop around a bit in addition to running your numbers. 

You can create custom maps to mark areas of interest, track properties you're considering, and note key amenities like schools, shopping centers, and public transport.