Industry professionals are biased towards what makes them the most money, understandably, because why else are they in this business but to make money? 

Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

You should consult a tax professional for an answer based on your unique situation, this is not tax advise just general information.

Thanks Sarah, I don’t see much house hacking going on in Essex or Dundalk in terms of listings on Zillow or FB so my concern would be finding professional adult roommates that want to house share in that area. i’ve been following a lot of the midterm rental groups in Facebook and the consensus is that contracts have decreased significantly and hospitals are using more local labor pools.

Readers should seek professional advice.

Estimating is both art & science and FWIW most professional estimators rarely get it spot on, usually operating within a Delta.There's tons of estimating books, software etc.

Consider hiring a Property Manager to manage out of state properties.

I’m a professional civil engineer with years of experience in construction and entrepreneurship.

You would need to hire a leak detection company to find out. 

You will also discover the warranties don't cover as much as you think, and claims are often denied.Home warranties are so bad that most professional property managers will not manage a property with one in place.