To do this legally, I know plans need to be drawn and submitted to the Planning Board.

How much are you having to pay the management companies?

@Itay HeledFirst Airbnb is a company.

Just google all the property management companies in your area.

And if you are need of MTR management services, my company, Island Stays Hawaii, provides premier STR and MTR management services.   

I understand this is not a requirement, but I have never received a damaged unit from an inherited tenant or any legal issues.

@Andy Ptak when jumping into the industry you have a few choices:1) Start at the bottom2) Leverage your experience to convince someone to give you a chance3) Decide between:--- Big companies who will usually start you at the bottom--- Small companies that will more like to a chance on hiring you for an above entry level position.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

With technology and the right culture property management companies can be successful with a mix of local and remote team members. 

thanks for your time and help 1st off, full disclosure here, Rent To Retirement advertises their properties on my Investment Properties For Sale Show, so I am not a totally unbiased opinion and it's only fair that I tell you this up frontHaving said that, outside of running my show for people like them, I also own a property management company in Northeast Ohio and have worked with 1,000's of out of state investors over the years.I say all of that to say this, the overwhelming majority of negative reviews I have seen on them are very similar to a lot of negative experiences investors have with my property management company and others like it that I've worked with.