Quote from @Chris Seveney: @Charlene Kingsnorth have you had an sec attorney also review what you are doing as if you're are having multiple people as part of a loan participating in it depending on the state this could get you in hot water - so be careful  good point Chris some state allow fractionalized deed of Trust mortgages other do not or require PPM like documents prior to offering them..

Taylor sent multiple email inquiries to our insurance provider asking what risks their policy covered.

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

That sounds like massive renos (ie new floors, painting...).Yes as you acquire more properties, the chances of having multiple vacancies (no matter how leases are staggered) increases.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

Typically, the same applies to LLCs where you and your spouse are sole members (single or multiple member LLC).

There will be more wear and tear and multiple headaches with several different renters.

Generally there are multiple units for each "zone" if you will when I've seen them installed.Regarding your problem at hand, I personally would simply adjust your plan to move and make your initial plan to get the current issues resolved, while costly now, in the long run holding onto the unit will likely pay off. 

Quote from @Mitchell Gunlock: Quote from @Cliff Benner: Looking for Tips on how to find places that have multiple cabins or additional dwellings on a property that I could live on and run.

Extremely communicative and Bob spent time over multiple phone calls answering specific questions I had concerning the deal.