I love the flexibility they offer for traveling professionals, military families, or folks in between moves.My main questions:Have you noticed increased demand for midterm rentals in this area, particularly from military personnel at nearby bases or healthcare workers at local hospitals?

There are tax benefits to running everything through an LLC, but again, seek advice from a tax professional.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

Start with friends, family, and professional contacts who understand your work ethic and track record.

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.

•If your goal is stable long-term tenants, you may want to target young professionals or grad students who stay year-round.4.

Readers are advised to seek professional advice.

Quote from @Andrea Lucarelli: I’m interested in beginning my REI career with purchasing a SFH or condo in Cleveland area (safe neighborhood) to list as a furnished rental for travel medical professionals, supply corporate housing needs, or house temporarily displaced families for insurance companies.  

They will get the highest price and the best terms for their property by marketing it professionally and exposing it to the maximum number of retail buyers, which means putting it on the MLS with an agent.