He knows the areas that you can legally air bnb, what specifically the property is going to need to maximize bookings/ROI, and has the property management contacts to optimize the ROI. 

I’m currently facing a similar situation and realized that I wasn’t using the right resources or consistently marketing to a single, optimized list.

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.

Where if they were using those funds to dollar cost average in marketable securities, they could keep 100% of that capital deployed and be asset allocated optimally based upon their retirement horizon. 

Id love to get a few more properties under my belt before the next recession so that I have my processes optimized and ready to roll when the deals come available.  

Note if the plan is to Owner occupy, it does not need to be an optimal Investment.  

Continue exploring various strategies to optimize your purchasing power and minimize upfront costs.Using an FHA or VA loan for MFH acquisition can indeed be advantageous, offering lower down payments and favorable terms.

However, I recommend optimizing your listings on Airbnb and vrbo first.

So as a listing agent/broker I will need to be more optimized for this marketing and processing of inquiries. 

Have around 10 units self managed and looking to optimize my business systems to be slightly more scalable and automated.