As far as STR goes, you can house hack the property that you first buy (in a single family home or in your unit of a multifamily property) and potentially do short term rentals in all of the other units or in your exiting property.STR as a way to invest is getting more challenging currently as supply of new STR inventory has been outpacing the demand for STRs.

Our inventory is so tight, that the market does not give a discount for condition and without that whats the point of a serveral months long rehab project if you don't create equity.

Worcester MA has been a hot market for the last 4 years or so, a lot because Boston is so expensive and the uptick of Work From Home. 

As far as insurance, as you probably know, it can be complex. 

As far as the activities available in the area, it seems like most of them would be seasonal.

As far as our experience, I think it is a great strategy!

Just a heads up.So you calculated out you need  $6 million worth of apartments to hit your goal.A commercial loan may require 20% to 30% down in cash, cash reserves, working capital, and closing costs.You will also need earnest money cash.The lender may also require certain repairs to be done Shortly after the loan is made.The lender may also require the Property to be stabilized as far as occupancy percentage is concerned, leaving little on the bone as far as sweat equity.Good Luck!

Colorado is quickly becoming on par or maybe even worse than California as far as landlord/tenant regulations. 

This is so helpful!  

-Sam born & raised in the area, also as far as leasing agent, we’re not like New York or Boston, you should be fine just leasing directly through Zillow.