I just wouldn’t spend a lot of extra money providing what for me has been essentially a break even process.

Loans are typically amortized meaning the percentage of interest paid compared to principle paydown is highest at the first month. 

HMLs enable quick acquisition leverage which is essential in competitive markets, and offer flexible qualification criteria, focusing on the property's potential. 

Have you considered how living in one unit and renting out the others can essentially let you live for free?

As others have mentioned (besides the essentials like rates, mortgage, and maintenance), it's important to consider utilities, insurance, property management fees, taxes, furnishing, marketing, and legal requirements.

Having a team in place is essential to long-distance investing.https://www.biggerpockets.com/blog/core-four-real-estate-team

This is essentially a much lower-risk BRRRR, since you will be living in the property and using owner-occupant financing, and also able to do much of the work in your spare time (if you have any) on nights and weekends.

Comfort with your decisions is essential for moving beyond analysis paralysis and taking action.

If we were to buy something in Lake Nona, it would obviously not cash flow as we would have her move in and essentially just help a bit with the mortgage, but how is appreciation looking in that market? 

When you put it in a spreadsheet and add in the interest to the principle every month it ends up being 30% annualized.