Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

A property allowing one-night stays may be more prone to fraternity parties and similar.

I've self-financed deals my deals, financed them with a HELOC and used third party lenders as well.

@Geoff Engel If you don't want to be a landlord but still want to be involved with investing you could be a private money lender for flips or in partnerships and bring the money to the deal.

Make sure to verify any information from a party that doesn't have any advantage of you getting their services before making a decision.  

There are a plethora of CT based real estate Invetsor meet ups you should get involved with.

Most lawsuits against landlords involve wrongful eviction, security deposit disputes, and Fair Housing Violations.

I am also involved in management at one of the largest STR property management firms in Cashiers.

Quote from @Ryan Konen: You are correct that comping software like Privy, Propwire, and Propstream primarily rely on public records for their data, such as county assessor records, MLS feeds, and sometimes 3rd party aggregators.

Because buying a house in excellent condition and then totally changing the layout can be expensive, especially if it's involving load supporting walls.