I bought a single family because I thought I could house hack in the same way as a duplex and in ways it certainly could have and did work but I didn't expect the relational aspects of having people living in a property I purchased.

Also--similar to apps like Facebook and Twitter--I can almost guarantee that a larger pool of people would seamlessly utilize their phones to vote/like and comment on the forums. 

I would check and see how many 1 bed and 2 bed options there are and what they are priced at because most folks will prefer the full place to themselves so rooming 2 people together could make getting bookings a bit more difficult (not always the case but something to consider)

My current situation is that I always flip with other people’s money.

I almost never get calls, most people send a message via Vrbo or Airbnb if needed, but it it much more common for them to just instant book with no questions.

CT isn't cheap so if you plan on doing it there you are going to surprised at how poorly you do. maybe in the suburbs I'm not sure but as much as I know people call us from CT and everyone is rich and has lots of money and things are expensive out there. build to rent is a great model. we build 3 story walk up infill and keep it to the residential side. 3 units is the most units before it's commercial and you need engineering, etc. check comparable and things liek that. we came up with this design a year ago and we sold 10 if you want to talk further please DM me happy to connect. there are some great build to rent conferences. we went vertical not horizontal with it to save on build costs and design to fit on any infill lot. this fits on a 3500 square foot lot. most lots in our area are 30x120 or 30x150. in miami where I live now they are 50x100 or so. but any infill lot we can pretty much get this one on. there are some great build to rent conferences coming up too that if you like this topic I'd recommend attending I'm sure you'd learn a lot.  

Only thing I'd say is that I've seen a slight tightening of the market as more people hear about the model.

Common problem, no easy answer:(We try to allow our owner clients to arrange their own maintenance, but have learned the hard way there MUST be limitations:1) They can't hire our people!

We are a good company with incredibly hard-working people.

You're already half way there by asking people what they want to hear.