My biggest fear as an investor (and father of 3), is that I'll overextend myself and end up in the same position that a lot of people were in during the crash. 

I hear some people think we are going up still and some think we will be crashed by this time next year. 

Took some time off during the crash but I’m not a newbie.

Yes, a win for them if the deal goes well, a loss for them if the deal crashes and burns even if no fault of their own. 

so predicting a crash on the peninsula has been great sport now for the last 4 decades.. the biggest crash happened in SF in 89 to 92 prices did crash some then.. but then made new highs by mid to late 90s.. and now with TEch fully entrenched you have a world class city with no peer.. prices are taking a breather ..

Or are you on the sidelines waiting for a crash?

We've seen a lot of new investors since the crash in 2008 - 2010.

Also in the next 10 years we will likely see another crash.

You rarely hear from those who crashed and burned from REI.

Except that with the market being so hot right now and with the way that Vallejo and all of the East Bay crashed in 2008 I would be a little bit worried about buying right now.