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?"

Believe me when I say that I feel your pain.  

I'd like to save him that pain).

FSBOs are a pain in the arse.  

If you do your own repairs, than it will probably just be a pain.

They can be a pain, and yes some are slower than molasses in December, but usually they make sure the paperwork is right and I have never had to argue with a bank on how they come up with a payoff, or interest I have paid.  

@Todd Simmons, plenty of flipping right now but all the flippers I see are local investors, much easier than doing from out of state which I'm sure some people are doing (like @Leo Furest), so if you want to get in the game here in Detroit make sure you have a great team otherwise your experience might be a bit painful. 

I’m a user experience designer by day (i design apps and websitws) and (selfishly) am wondering what kind of pain-points or potential apps, websites, or other digital products you wish existed!

For now reading and continuing to go through the growing pains is what will be needed. 

It's great because I essentially have infinite returns on those properties, but it's also a pain to do his statements every month and now I have to share my [tons of] equity with him.