Also look at those Vrbo and Airbnb calendars and see how full they are and what nightly rates they are getting.Should be easy from here to see if a new property would pencil in or not. 

Brand new house.  

For a quick turnaround during the holidays, that rate might reflect premium timing.

As others have said, the best thing your son can do is run far from this deal, buckle down, save his pennies (he probably already is doing this), house-hack, and improve a property with sweat, hard work, developing a DIY skillset, and self-managing tenants. 

But I bought 3 more houses with the cash and now cash flowing $3000/month vs only $1200/month with that one paid off house.

What is the interest rate on your student debt? 

For an example, we Googled, "hourly rate for handyman Austin, TX" and got this:AI Overview: As of January 2025, the average hourly rate for a handyman in Austin, Texas is between $25 and $25.28.

I have 7 MTR and my income is 1.7x my long-term rates ($1200 vs $2000), but that is very specific to my properties, my location, my business model, etc. 

The December 2024 report from the Austin Board of REALTORS® (ABoR) shows stable housing prices and balanced market conditions in the Austin metro as we reached year’s end.

LTR and MID term are hot now as well, we have more people that want houses than houses to rent to them.