Property manager and assistant property manager (as your direct contact)cheap, fast, and good - typically you can only pick two

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.  

Slip and falls are a leading liability concern a property owner should be aware of and snow removal is not something to cheap out on. 

It reminds me of one of the TAX sale how to traveling freebie events that came to town last spring..

Living in a great travel destination like Sonoma you should consider a duplex or triplex and operate the other unit(s) on AirBNB, VRBO, etc.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.

If you need income that'll be a certain set of options if you're trying to free up time and not be responsible for property management because you're planning to travel in retirement that'll be a different direction.

If they can get a property dirt cheap, you are still going to see it at the 80% of ARV like he says.

There are many more and many more personal goals such as getting married and starting a family, adopting my first GSP dog, traveling to Wyoming and Montana and spending more time in nature, just to share a few.

Investing in "Cheap" cities are not always cheap on the long run.