Due to the decreasing level of low-rise inventory, it is reasonable to assume that some of the pent-up demand has shifted to the high-rise market in the form of new unit sales, resales, as well as increased demand in the rental segment.

What was different about 2016 compared to other years' is that you could actually find quality product on the MLS and there was choice in the market (for a while), this has since really dried up in some segments.  

That sort of begs the question, is it really an external market influence - sellers asking for more money or is it an internal market influence - your model doesn't price that asset/segment/population as well as it use to with experience under your belt?

Additionally, I work full-time as a commercial real estate broker focusing on the multi-family and hospitality market segments.

What the main segment ur looking to start with?

As to the lack of senior housing, it's one of the fastest growing segments of the market.

I was annoyed with the segment because they acted like all landlords are bad guys who show up in housing  court with lawyers because they want to take advantage of poor tenants and never once mentioned the fact that the courts require owners using LLCs to hire a lawyer. 

Try breaking down the year into 90 day segments with goals.

I once painted a house in tiny segments over a winter.

Perhaps you could find somebody somewhere that is local (not in NYC), that already invests/works in this segment, and has a few bucks to put in, and partner with them?