Just looking at Zillow I’m having a hard time making the numbers work between prop taxes, insurance, management on 20% Down vs cash currently earning 5% (albeit that 5% going away soon with rate cuts)  To be completely honest, there's not much right now that will give you decent cashflow without getting into a full rehab.

Use the ge benefits that you have earned to their fullest. 

The mortgage payment is $1,000 on each house, so you earn $500 per house or $2,000 monthly.

Dumb Debt also means that the owner takes on recourse debt and personally guarantees it instead of non-recourse debt or other people’s debt (OPD) or cross collateralizes it with highly appreciated assets with low debt to value ratios.

However, I think for the average person this is probably not true. 

Relatively small amounts of interest income ($1600+ per year) is the highest taxed form of income I have found if you have kids at home.After earning a few grand in interest, It takes away my child tax credits and gives me an effective tax rate of 70%.   

I am not sure what type of real estate investing you're considering, but it sounds like, with your family and busy job, you won't have a lot of time to be hands-on or personally involved. 

Offered to intern/work for him at half the pay as his personal assistant if he would teach me everything he knew.

Then they receive the money and you still keep your money and earn money on it.

To beat 5.25% mortgage rate....the corresponding, offsetting stock market return would be at least double that...To answer your question requires (1) knowing what risk adjusted return you will be able to earn in the future (2) knowing what interest rates will do in the future.