I started again 4 years ago and have about $3.4M AUM now but it’s nothing compared to what could have been had I played my cards different 27 years ago.

Are the closing costs a deal breaker compared to having cash on hand for any potential opportunities? 

You're probably buying at higher rates, but just run the numbers, see what you can afford, and compare potential monthly payments to what you could get in rent.

but then again you will ALWAYS overpay when you compare it to doing it yourself.

Look for the same limits or better and then compare costs.  

Look at the expected returns for each deal and compare the opportunity costs.

Comparing this vs buying an older property that will take a decent amount of work and time to bring up to speed.

What about anything else they need to take into account and have you compared against others?

.- Tourism and Hospitality Businesses: Some local forum post mention that Cookeville has a strong tourism and hospitality industry, which could drive demand for furnished short-term rentals and extended stay hotelsI also checked to see what other listings are available and found about 4 comparable listings ranging from $1300-1500/month.

These are pretty standard terms, comparable to commercial lender.