We’ve got about 30k liquid cash to invest and could potentially double/triple that as needed by selling some company stock (havent done that yet because the stock is doing well but could be convinced for the right deal).

My plan for most of the money is to invest it for retirement in stocks and bond funds.  

The question is: should we wait a little bit more for prices to drop a little and meanwhile invest in stocks or pull the trigger and buy a house? 

Analyze and optimize your personal finances, and invest in less capital intensive vehicles (index funds, blue chip dividend stocks, bonds) to save up for a bigger down payment.

But enough about philosophy, and on with the tale.In 2008, the stock market had crashed, the credit market had imploded, and the housing market was sliding into the into the toilet.

You're trying to analyze a REI in the same way as you would another (stock market) investment...and you can't. 

Have a main stock line - sewage - leaking in my property, need a plumber that can inspect it w snake / video and fix it without breaking walls. 

Depending on how much tile/flooring you need, I would check out Lowes and HD for their discontinued stock or whatever they have on sale.

I figured it was time to start exiting the stock market and use some of the money to purchase a cash flowing asset. 

We go really cheap on some things, like paint,  towel/toilet paper holders, and go higher end on things like faucets.. as others have mentioned, it's an art and you have to find your balance.Also... so  many people forget-- this is someone's future home, this isn't a mutual fund/stock, so you need to focus on what things will make your tenants happy!