It depends on your plans for how you will invest the money, but I was in a similar situation and opted to do a HELOC because it offered me more flexibility.

I am sure you can find similar properties up there to gauge rental prices and interest but if you plan to use it on popular weekends you may fall short of your expectations.If this may involve many family members I think the first step would be to make sure everyone is on the same page with whether you are going to rent it, when you will be trying to rent it, and how long you plan to hold the property.Many of these seem to be setup in a family trust or Family LLP with an operating agreement which I am sure you can handle. 

My wife and I are similar that we are trying to get to that point with by and holds as well.

Similar situations. 

Does anyone have similar experience with other Property manager companies?

My HOA is going through a similar process of comparing vendors right now.

One way to get around some of this is to physically connect the two structures with a covered walkway or similar type structure.

I liked your post and felt like we might be in similar mind sets regarding real estate.

I am comfortable in the towns/cities that I am researching in Mass, I just wonder if I can do similarly well in Florida, Colorado, Texas, but with half the cost!?

Instead, use BP and other similar resources to build yourself a local network separate from those providers that you pay for services.