.- I'd start with the end. 

I imagine this will help me with a refinance in the future.

California has seen huge uptick in home insurance, I'd imagine Santa Cruz has a high fire insurance

I'd save yourself from the headaches and just buy it with a DSCR loan.

@Shafi Noss Yes, I'd love to hear more.

A great CPA who specializes in STRs can confirm this and help you stay compliant.About That CPA…Honestly, I’d recommend finding a new one.

I’d like to put as much down as possible with  conventional loan.

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.

As much as I'd love to rehab the properties to boost the ARV (which was the initial goal), funds are tight right now to do that so as-is is the way for me to go.Absolutely.

@Anthony MurphyI’m an affiliate for both of them and at this point I’d recommend PropStream over DealMachine.