Do a strict analysis and decide if this property is worth keeping.

Our end goal is to own both a property strictly for rental along with a family vacation home in a sem-rural setting on multiple acres.

Gather as much information as you can, and decide which discussed activities make the most sense for you to add/adjust/remove from your routine.

They invested time and money to obtain theirs.Yes, sometimes the policies are too strict and the charges are excessive - but an expectation of free service and advice, no matter how quick it is to administer, is wrong. 

Strictly rental revenue.And beware of PMs out there that offer you a cheap % management fee, only to charges guests $ hundreds in extra fees (booking, damage, cancellation, etc.) that they pocket and don't share with you. 

Strict lead laws.

Are you wanting to do any fixing (through BRRRR) or just strictly buy and hold? 

Based on the Boston market and my price range I have been looking at 2 and 3 bedroom condos.I have strictly been looking in the Boston area bc I have knowledge of the rental prices, and thought it would give me the best opportunity to cash flow.

Now that does not include things like taxes, insurance etc. you are paying, that is strictly the cost to foreclose.

The biggest thing I have learned on this journey has been just how strict you need to be with GC's.