My answer is: doesn't matter-- they'll seek to avoid the conflict and I bet for $2500... they'd pay. now the real question in the OP's case is "is a search of water department's records USUAL AND CUSTOMARY prior to title policy writing and closing on her jurisdiction?

Your "opinion" doesn't help me defend MY professional appraiser opinion about the value of your property, but if you provide me data I'm not aware of, or haven't thought about, etc, maybe I can justify a different conclusion.Here's a thread where I posted a more detailed answer to what to do if comps are lacking.

Do not try to qualify as a real estate professional with a w2.

I've been all over this country seeking out quality educators.

Personally, I can't imagine achieving returns like that with professionally managed equities & after 40 years of JUST equities, (my still working @ 70) BIL's financial results are nothing like ours. 

How would a professional business handle this?

I'm about to start short term rental for travelling Nurses (travelling medical professionals).

While I work towards becoming a professional engineer and working with developers, my goal is to own a couple multi-unit properties by the time I’m 30.

Do you think I should talk to a professional CPA who specializes in real estate to get the best time frame on when and how to so? 

Start by being thorough in your research and seek input from experienced professionals.