I would focus on establishing a career base, building a strong credit score, and eliminating as many personal expenses as possible (I too had to sell my shiny red car and "put my money where my mouth is").   

You'd be amazed at the power of word of mouth in RE!

I'd love to hear from anyone who has come to these conclusions...I'm feeling a little doubtful, like I'm missing something...but honestly, I'm pretty sure I'll be much happier and productive with a high end, lighter laptop.

I got sick of complaining about them and decided to put my money where my mouth was.  

I get all my jobs from word of mouth from previous clients.

(And on top of that, if he's a typical hand-to-mouth contractor with debt up to his eyeballs, he may not have assets enough to satisfy a judgment even if you get one.)It would probably be better for you to chalk it up to an expensive learning experience (unfortunately, there are lots of those in this business), try to analyze how you ended up in this situation and how you can prevent it for the future, and drive forward with getting the house done and on the market while you still have time before the holiday slowdown.I wouldn't let him get off unscathed, though.

Ultimately, I’m happier with medium to long term furnished rentals with clients found on Facebook marketplace, zumper, Zillow rentals (hotpads), cozy, etc. than having all my money coming through Airbnb.

Here's why;You won't be seen as a serious buyer, but as a fisherman for dealsThe Realtors will despise you for clogging them up with low ball offers in the pipelineYour reputation goes with a contract offer, banks will start ignoring you if they see you low balling them on all their properties.If you make reasonable offers, can you put your money where your mouth is, can you perform on multiple contracts at the same time?

Income, is it reliable and sufficient to pay all of their bills, feed the mouths in the home and then pay you?

Youcan close your mouth.