I understand Vermont has slightly more stringent regulations to contend with but it would also be closer for us geographically and thus potentially easier to manage. 

In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

Federal Laws Prohibit Discrimination of 7 Protected Classes, Massachusetts has added 8 more:-02.Always know more of the Rules/Laws/Regulations than ANY Tenant.

., the specific procedures laid out by the SEC in Regulation D.  

This is a highly regulated activity by the CFPB.

Using a large RV or boat for business purposes offers potential tax benefits, but it's essential to navigate IRS regulations carefully.

A tax advisor specializing in real estate can help you navigate deductions, plan for 1031 exchanges, and ensure compliance with ever-changing regulations.

I saw an example recently in Bloomberg about how local regulations can really shape a landlord’s experience, from what I’ve heard.

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

These programs offer options for less money down and in some cases DPA - Down payment assistance.As a banker for over 18+ years I am very skeptical when I hear a new name in the business only because its become tougher to lend with all of the new laws and credit/insurance requirements and regulations.