Biggest issue with booking.com was that I really felt their interface was terrible and took too long for a property to go live.

LTV is the biggest think I am seeing taking a hit.

The biggest difference for us real estate investors is that 2008's crisis was caused by real estate. 

Maybe you can get him to provide an incentive to close early. 

Biggest lesson learned was hire the right people first and get it done quicker!

Personally I would work on the debt side first, since purchasing a property is probably going to be the biggest investment of your life.Although you always hope it goes smooth with a rental, I've definitely had times when someone stops paying and you have to evict

Biggest take aways was learning how to find a really good agent because it makes a world of a difference and  also learning to leverage as well as build relationships with your team from out of state. 

The biggest thing with land is lack of liquidity, unless you can buy it for 20 cents on the dollar and flip it for 50 cents, it could take a long time to sell if you buy at a market/retail price.

Biggest Winners/Biggest Losers -- As always, sideline investors regret sidelining opportunity. 

A drive-to vacation, where the biggest expense is the STR rental, is going to be preferred by many.