The town treats it as a commercial lodging property so it's exempt from heavy-handed local STR restrictions.The sellers have been open for biz only part time in their retirement.  

So here I am, looking to connect, meet other investors, and learn everything I can, so that I can make a good first decision in my real estate journey.

Hemlane offers property management through our innovative model where we send 100% of the rent to you so that you can control and approve expenditures as well as have full transparency into the day-to-day so you always know what's going on and can make key decisions. 

Remember, no system is perfect, so avoid the temptation of constantly chasing after the next shiny object.

Are you skilled at marketing - if so potentially you could market yourself as a virtual assistant for folks in the real estate world so that you can learn from a lot of folks at once? 

 Thank you so much for asking this question.

@Aramazt Tanashian I'd be cautious as no expert works for free.So, either this person talks a good game, but doesn't know what they are doing, OR they are hiding how they'll make money finding you a property & rehabbing it for them to manage.EXAMPLE: contracting companies make 20-40% markups, so why would this consulting company not charge to handle rehabbing a property for you?

The question I have is, I would like to plant a privacy hedge (Clusia) around my backyard, it is currently fenced, I'd plant them small because they're much cheaper,however, I know 2-3 years down the line they're going to require trimming every so often and that will need to be paid, the question becomes, is this something I should do or should I keep the property as plain and maintenance free as possible? 

it is in Massachusetts so appreciation is there but cashflow has always been lacking. 

This is a new PM to the OP so initially trust but verify.