I thought the regular "free" Stessa account was ok.

When I'm figuring out how to price an Airbnb I always cross-reference AirDNA or PriceLabs to get an estimate on what the income would be.

Do you check Landlord references?

@Placeholder PlaceholderOne word of caution I would advise: If a community or local government is enacting restrictions and also regularly enforcing them, then its often a reflection of the local community sentiment which increases the chance of a neighborhood or nearby resident calling you in if they think you may be running an STR.

I've bought a ton of homes pre-foreclosure and at auction, happy to be a resource on that stuff, plus we just launched Bid Pirate, which is the one place online for NH, where you can see all the upcoming foreclosure auctions in one spot - you can learn a lot from the regulars at the auctions........ get after it, sister!

I spoke to several of the insurance agents we use here in the Disney area and they have all said that policies are regularly being written and by all they hear, will continue to do so. 

Get at least 3-5 quotes and check references.

@Kyle Mccaw Okay yes are you referring to FHA loan?

Then I consider letters of reference, cosigners, and added security deposit in order to meet approval. 

I'm not saying you'll be working a lot all the time, but you'll regularly have late-night questions from people checking in, for example.