Actually in Pewaukee, so also easy to get to from Madison.

This is basically what I made for myself:So every morning I get a report of everything new that hits the market in LA/Ventura, and I can just click the google links, check it out on RedFin/Zillow, and if it seems promising, fully underwrite it (using tools and/or manually), then offer on it.Don't try and come up with an auto-offer estimate, you can't tell the visual quality of the home or how much the construction will be, etc, stick to estimating values of renovated and distressed property in your tools, make it easy to fill those comps/value metrics into an underwriting model/proforma, and let the end users tweak numbers/select comps/etc so they feel confident in everything.

So far the quoting and signing on process is fast and easy. 

In my experiences, it really comes down to the tenants that create either a management headache or a super easy investment.

Seems like easy savings. 

I also know finding a quadplex as a first property in Orange County isn’t going to be easy, but I’m open to hearing people’s thoughts.My goal isn’t to turn a profit right away—I know properties here might not have positive cash flow for a few years.

What you want is, as they say: relatively simple, but not easy.

That it is near you is good, but find out how easy it will be to sell. 

Using automation can certainly help at scale for easy things, but if you have one STR and can't be bothered to respond promptly to your guest, I can guarantee this business will not go well for you.

A handy search bar in the upper right makes it easy to find previous discussions, blogs, podcasts, and other resources.