I own property out there but we are self managing.

As a carpenter I focus on the wood itself, but there are differences in everything.

I think you're spot on in there not being an obvious decision.

But there's a lot to like about the Portland suburbs as well, it just depends on what you are hoping to achieve, the skills or assets you bring to the table, and your timeline.

I also require my tenants of any length (I only rent for 30+ days) to have their own renters insurance for their own belongings so I don't see any big issue with having your part-time tenants get renters insurance and then making sure that your own homeowners policy is aware that there are others living in your home but that they have separate renters insurance.

There is no such thing as just simply being lucky.

For example, there's an Employment Verification Form, Forwarding Address Form for Deposit Refund, and so forth, that you can request your tenant to fill out.I want to make sure I'm not missing anything (as well as protecting myself) but also don't want to over-burden the tenant. 

Does anyone have investing experience/successes/advice on what is doing well there?

So, the answer is: there is nothing that clearly prohibits DIY cost segregation reports.2.

If I understand this right, your 2 out of state LTRs have no connection at all to your LLC, so you aren't getting any benefits from the LLC there.