My goal is to diversify with an investment that generates steady cash flow, even if it requires a larger upfront investment and lower overall returns. 

Here in in the Disney / Orlando market, accommodating larger groups is a must.

Personally speaking, from an investment broker and investor standpoint, I feel single family investing is the riskiest in some investment ways in comparison to larger investments due to the fact that it only takes 1 repair or tax/insurance hike to put you under or lose all income.

However, it restricts corporate growth.Syndication, on the other hand, involves several investors funding larger deals.

The ARV on small multifamily can be a bit tricky as most appraisers will like to use the comparable approach as to an income/NOI approach typically used by larger (5+) multifamily properties.

Eventually, I am looking to possibly expand to larger commercial properties with 5+ units. 

I would start with those that have been around a long time and are larger in size.

I feel a loss of direction and that makes it really hard for me to focus and build.Do we keep at building a portfolio of small multi family (very abundant in my market, very rare to find anything above a triplex for sale), with plans of selling the portfolio and 1031'ing into larger properties? 

Their units have exceeded expectations over the past two years.Danbury should be fine for house hacking with having a larger number of mulitfamily properties within the city.

We're in the larger multifamily space, but regardless location is pretty universal.