Thanks @Theresa Harris, @Jake Andronico and @Bill B. for the tough love comments :-)It all makes good sense.  

Shelly and I have always been driven to help people, especially those facing tough times.

As I pay contractors, for materials, etc., I add it in the check register and class is to the WIP account.

Looking for advice - purchased first STR 2023 and we qualify for active income based on rule 3 of the material participation test.

But what you’re encouraging is that when I am 23, I should use the first 4 or so years just building a portfolio of LTR’s and then when I am 27, look into leveraging STR’s to meet the “Real Estate Professional Status” and “Material Participation” the IRS outlines, correct? 

@Skyler Shively, as mentioned, it is a tough niche to find a lender for. 

retiring on cash flow is a pretty tough thing to do for most folks full stop.to me to do that its highly dependent on your location and price points.And how much capital you have to start with and or your day job to allow you to scale.

Sorry to hear about this – a $14.5k repair is definitely a tough situation.

Are there any good materials (books, websites, etc.) you might recommend? 

San Jose/Santa Clara will be tough market because of the price points.