I'm on my second house hack (condo) and then my wife and I house hacked our ADU/Main House.

I know the question is mainly focused on what sorts of special protections you will need as a landlord with a lease as opposed to a longer-term AirBnB booking, so let me answer that first. 

I'm doing everything I can to learn about real estate investing (mainly via reading), and there are concerns I have about my future in this field, that I want some more clarification on, and better yet creative solutions.

😄So I’ve mostly been looking at basements with a walkout that I can finish and that can be separate from the main house.

I give them full time jobs at my PM co with benefits :)But to hire on a contract basis - mainly echoing from above - I would go to Thumbtack, TaskRabbit, Local FB groups.

Did you run into any unexpected challenges with the layout or structural elements?

You can also ask the tenant to sign an estoppel, which essentially has them verify the rent they are paying.As for expenses, the main areas where they can go awry include property taxes, which you can determine on your own; the mortgage, which you can also calculate; insurance, for which you’ll have a quote beforehand; and utilities, for which you can obtain the bills from the landlord.

Very few people go to the main page without a destination and dates in mind. 

Our main issue is financing.

We do Self Storage mainly, but the above fits your background better.