This is a big one because if people must sell, they’ll be further adding to the inventory and price dropping war goin on in the marketplace causing more downward pressure on asset prices.Unemployment rising — Many people will lose their steady employment due to economic challenges during a down market.

I am trying to get a sense for what is involved in undertaking a project like this in either of these markets, and whether or not it still makes sense in today's economic environment. 

A concern I have at this time is that overall the market is slowing here on O'ahu and with some US and global economic challenges, it seems like there will be better investing opportunities if one is patient.  

Check local newspapers, business journals, economic development commission, chamber of commerce, etc. to find these events.2.

I imagine there's some improved economics for both sides.Further, would it be possible to combine efforts in a given region and have 10 property owners with 20 units each bid out their PM contracts as a group?

The holding LLC would have contracts with each subLLC to manage it --- basically its an in-house Property manager..I think many would put about $1mil of current value (equity isn't the correct term since you are probably leveraging so your equity is really small) in each LLC to economize. 

I do Houston only because I grew up here and I like the economics of the market.

Buy in a primarily owner-occupied neighborhood to attract tenants who are a lower economic risk.

My undergrad degree is actually in RE micro-economics and I studied with the late great Chip Case of the Case/Schiller Index fame, so...not new to the thought space of real estate markets.

Unfortunately, if we dig deeper in both the history of rent control and the economic fundamentals at play the idea of bringing this piece of legislation to solve rising rents single handily falls short of it’s intended results.⁣⁣Think of where rent control is currently in force and where the rental market is currently fairly open, think of cities like New York, Toronto, Vancouver, San Francisco etc.