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.

My goal is to attract standard medical office tenants who do not require specialized equipment—such as Primary Care Physicians, Urgent Care Clinics, Chiropractors, Physical Therapy & Rehabilitation Centers etc

These are the people - in my opinion- that need loan brokers the most, since they really don't have a grip on the market - and are thus more susceptible to agreeing to suboptimal loan proceeds / rates / terms. 

I've got properties in (2) towns currently that are around 10k people in each town.

Are there property managers that specialize in these kinds of unusual properties?

I don’t have a specific recommendation off the top of my head, but for HOA/condo insurance, it’s usually best to start with a broker who specializes in multifamily or association policies.

One more tip – people remember stories that trigger their emotions.

Essentially I am looking for a clean way to organize everything as right now its very messy with how my current accountant is working things as he doesn't specialize in real estate.

Quote from @Bryan Martin: I invest and live in Springfield and also run a CPA firm that specializes in Real Estate investment. 

Check your insurance, I’ve seen a lot of people specialize in renting to group homes or care facilities so there must be a commercial policy for this.