i dont know "when" if 2020 is right or not but i do personally think that these mega plex luxury buildings are going to feel some serious pain the problem is that theres still so much capital floating around trying to find yield that even if they take a big haircut on price or large vacancy ... there will still be appetite for the riskone thing that could put a big change in the market and probably not talked about as much is the Millennials will stop wanting to live in a box and will start wanting to move into a house.... suburbs that have been basically looked down upon will find itself going thru a renaissance we are already seeing suburbs starting to get things like trendy coffee shops, art centers, etc to make them more geared toward millennials ... this will continue and i think the "city living" in metros that are not nyc sf will see an influx to places i know what you are thinking "ok Alex sure... but what will be the catalyst will be for this change in behavior?"

Restaurant scene on Ventura and shops/boutiques seem to have gotten more trendy than before.

If the trend is downward, then sell now.

Instead carpet will get me to my next vacancy and then I do whatever the current trend is and toss it up for sale.

Trend is  south of 10 and then north of 10 and then north rail road.

I'd expand your search a bit and give a chance to some of the neighborhoods that maybe aren't quite the fun, trendy neighborhoods, but are close to them.  

The numbers with $$$$$ in front, tell me how the other data impacts the buyers/tenants.I collect "my" numbers, over the last 3 months to tell me what is happening now, and over the last year to three years to tell me what the trend is, map out all of this to find the micro-markets where the spreads work towards my criteria...and go from there.

An area in which there are lots of restaIrants / bars and turnIng trendy rapIdly wIth lots of old buildings in the area that can be converted.

The overall trend is still up.

Popular, increasingly trendy area.  1-4 miles from the French Quarter/Downtown areas.