You won't have the options that you have here in Austin, mainly because Portland is Tenant Friendly City and Pfugetville is Landlord friendly.  

The main reason is that it is not initially set up for a Real Estate business like other “real estate-specific” accounting software.

A couple thoughts on your question:I tell our STR investors in Colorado that their main goal should be to set up the right way right out of the gate.

We feel this encourages/trains good payment behavior:)We have several MoveIn Specials owners can approve like, free TV, Washer or Dryer (used), etc.Our main goal with MoveIn Specials is to stand out from our competition. - Just lowering the rent really doesn't do that.

If cash flow is the main goal, there are many other markets to consider before San Diego.

I'm a fellow real estate investor and I own properties throughout New Hampshire and Maine Southern Coast, I'd love to connect and bounce ideas off each other. 

Main question in other countries is ownership and taxes.  

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

I mainly use FCI and Madison for the majority of my notes.

The main criteria to evaluate this is when did you complete the start-up phase and became actively engaged in business?