Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Have you already talked to the seller?

A lot of people tend to mingle these things when they talk about "break even" or "cap rate", but that leads to a lot of confusion.Let's use some real numbers which may be easier to understand. 

He always talks about his deals being conservative, but there seems to be some big gaps in the underwriting, with the 2 deals I am in. 

You'll probably get some good ideas here, but I'd suggest talking to a real estate attorney soon and maybe run some of these ideas by them.

In talks on four different properties. 

I work with investors from California all the time that are able to find good cash flow in a growing market where the appreciation is obvious.I agree with @Jason Wray that many of the investors I talk with from the West Coast find that the markets in the sunshine belt work far better for their investments. 

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Also talk to local agents and ask for their insights.

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.