So, the terms of your lease should be catered to that, with very strict insurance terms, personal guarantees behind any company signing your lease, requirements that lessee handles all repairs and maintenance, additional security deposits, and I would go so far as requiring minimum review quality for the host, limits on quality of guests they can accept, etc.And to your point about Airbnb not doing background checks, you are right.  

I practiced analyzing a deal with my friend the other day and the ROI I got back seemed really high lol.

I highly recommend you paint the doors and trim.

This is a great strategy for high income earners as they can purchase a short-term rental get a cost segregation and slam a huge loss through to offset current years income. 

Others may disagree, but I would highly recommend paying off all of our debt and increasing your savings rate before investing. 

As we all know, interest rates have been very high these past years (7.5%-7.7%), and there are rumors that the FED are looking to cut the interest rates in 2024.

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

I built high-end custom modular (e.g. stick built in a factory and shipped) for a significantly cheaper cost per sq foot than it would have cost to build with a local builder.

I'd ask your engineer that question and say you honestly want to know (Hanlon's Razor) if he dropped the ball on this one or if he had a reason not to call/email DOT before pushing your final design through permitting.It sounded like he expected the possibility that DOT may flag the project and had a plan to respond. 

I highly recommend attending a few monthly networking events/meetups!