Found the right forum for me because I am definitely just "starting out!" 

Here's my situation: age 36 with a two family house in an extremely expensive suburb of Boston. I bought it from family members at a very steep discount so I only owe $189,000 on it at the moment at 3.5%. I live in the top floor and rent out the bottom floor. Unfortunately (or fortunately, there is some less headache upside) I rent the bottom two bedroom out to a family member for $1200/month. That situation will sometime change in the future and I will be able to update that apartment (needs a lot of work) and rent for around $2000. The house appraises at about $600,000 but would be worth more on the market because of the desirability of the location. I work a full time job - that's RE/financial picture at the moment.

The reason why I'm here is I met someone who owned a house in nearby New Hampshire. A log cabin close to skiing areas. He would use it himself here and there but mainly rented it on Airbnb. He had a property manager do cleanings and key drops and would just go up there somewhat regularly to supply toilet paper and other goods, since it was cheaper than going through the property management company for those things. He was cash flowing a few hundred dollars a month this way. Sounded like a great idea to me and it's been in the back of my head for a while.

So I have researched properties and Airbnb pricing and the NH laws for this and it seems quite doable. I am currently focusing on property management companies to see who is where and which ones are best. 

Does anyone here have Airbnb experience? I have listened to the most recent BP podcast on it, which was awesome.