If you’re feeling uneasy about the potential headaches, you might consider a local property manager who specializes in room rentals or shared housing.

Please consult with an accountant specializing in real estate taxation. 

As long as the ADU is under 900 sq. ft. and meets the state building code, there will be no variance or special permit needed, so no ZBA or neighborhood meetings.

Start small, ensure your numbers (purchase + rehab + holding + selling costs) leave room for profit, and build a reliable team (contractor, agent, lender).For financing, work with lenders who specialize in fix-and-flips. 

Special needs, recovery?

Check references, and ensure they have a reliable network of subcontractors for specialized work.Regarding whether to use one GC or separate them, the first option is more efficient for oversight, but it can come at a higher cost.

All good reading and listening, education is best and if you want to learn you have to ingest as much information as possible.I read many books that helped me, but my go-to is listeining to at least 2hrs of podcast with real examples per day.One very important things that "want-to-be" fails is to understand that real estate has many different specialities, so you have to focus your time in your real project.

Define your budget, connect with specialized agents/lenders, and start analyzing deals.Good luck!

Wondering if there are any good property management groups that specialize in this in this area?

Quote from @Frank Barletta: Yes.VRBO has its own Expanded Distribution Network which includes Expedia Distribution brands, such as:TravelocityCheapTicketsOrbitzExpediaTrivagoKAYAKOther affiliates that specialize in vacation rentals.I get < 10% of bookings from VRBO in my markets so this is my experience.