One problem Mass still faces is the lack of supply with reasonable demand.

demand? 

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

You probably do not need a lawyer to write a letter but you probably do need a certified “demand” letter to show that you have requested removal of their stuff before step 2.

I do get alerts from Redfin, unfortunately I'm not familiar enough yet with the lay of the land, what area's / zip codes are most in demand for rentals, things like that. 

With 15M + visitors flooding to Nashville every year, the demand for hotels and short term rentals is sky high.

The property is well located and in a area with high demands for rent based on the info dug up and discussed with multiple people this units stay rented most of the time and there is a high demand for rental in the area. 

If the landlord does provide a list of deductions and the tenant disagrees with the deductions taken for expenses and damages, or if the landlord has not provided such a list, within 30 days (or up to 60 if specified in the lease), the tenant may send a “Seven-day Demand Letter” to the landlord, itemizing the charges with which the tenant disagrees and stating that the tenant may sue the landlord for three times the amount of the deposit withheld if the entire deposit or the disputed portion is not returned to the tenant within seven days of receipt of the letter.

She loved making demands, bossing the handymen around, and having absolutely no accountability/responsibility for any damage she caused. 

Rental demand could even go up if banks start increasing their lending standards, which a lot have been doing already.