You're thinking far further steps ahead and weathering the volatility to reap likely more a fat-tails esque reward which likely does happen at the turn of the next inflation wave(not this secondary one coming up).From 08-16 you could do the former, from 17 fwd it's best to the do the latter.

The volatility of the markets and constantly changing guidelines have been the largest pain points from what I see.  

Also with the volatility of BTC I wonder how feasible it may be to transact 100% in BTC at a current state.

Lets say I make a $50k investment into a syndication, I am 100% ok with getting a 10-12 annualized return with preservation of capital and lower volatilty / lower standard deviation versus 15-20% but high volatility and high standard deviation. 

It's great to see interest rates "level off" at something workable for hopefully all parties...the volatility over the last several years has been tricky to navigate...Chicago hasn't had as many market fluctuations which has been nice.

For the market to be healthy I think that rates have to remain like this for at least a couple of years...Changes in rates affect the market so much making the industry too volatile.

In your case, if you have $100,000 on the sideline I don't know if I would necessarily invest all of the capital unless it is in at least a B neighborhood and play the long game, rather than invest in the more volatile markets and swing for the fences.

I stay away from the luxury segement, I believe it's too volatile.

We are seeing a lot of volatility with new listings, they either go nuts with offers - or don't get an offer at all.

Then when they leave it is very volatile for your business.