I'm also in MA and have been stuck in paralysis mode for years. 

Hence, leasing seems a viable alternative in view of rents in the area.

I know a lot of people who are in the wholesaling industry and what we are seeing is that texting won't be a viable marketing method for long at all.

Since you’re in research mode, getting familiar with neighborhood-specific trends will be key, some areas have strong rental demand, while others can be trickier to manage. 

This market is somewhat saturated, but there are pockets where STRs are still viable.

I personally do not care for their high pressure model.  I

It may not be the popular way as far as the Bigger Pockets community thinks, but it definitely seems like a viable, allbeit slower, way to get into real estate and build a little wealth over time.

You can setup a "guest mode" allowing the guest to enter their check-out date.

I bought the house for $22k if the bank was only using the $22k no way I would even bother investing in this model. I

Tiny homes often attract minimalist-minded renters willing to pay a premium for cozy, low-maintenance spaces, making this a viable niche in your market.