I recognize that (in the equity market anyway), it's quite difficult if not impossible to time the market and time in the market is more important than trying to time it.

That is impossible in San Francisco. 

Unless it is impossible in your situation, initially try managing the properties yourself for a while and THEN make your decisions going forward.Good Luck,Paul

Welcome to BP @Adam ObackThe bay area is very hard place to wholesale but it's not impossible.

Before I thought I had to drive around looking for distressed properties and then tried to locate the owner which most of the time was near impossible.

Finding a company with no cap is almost impossible these days.I've heard of Allstate and safeco covering up to 14 days for short term rentals in primary home owners insurance but both don't offer guaranteed replacement, they are only extended replacement up to 150%.I called CBiZ but haven't heard back.Has anyone ever used anything else or a per renter insurance thing...I saw one on the forums that was like $39 per booking.

Impossible to do that if you don't already know the value.  

I grew up in SF, the city is near and dear to my heart but they make it damn near impossible for Real Estate investors to make a buck.

Scary indeed, but not impossible to find a good deal like you just mentioned about the condo.

. $513 all in is tight (not impossible) on a 570.