Most would be better off with just a regular landlord insurance policy and an umbrella policy.

Assuming a similar scope of work for a 1000 SqFt house would you say say $25 a SqFt would still hold (maybe $25-40 with a regular handyman or crew). 

Quote from @Emory Clayton: I'm confused as to how to screen Sec 8 tenants compared to regular 'market rate' tenants.

Set up a clear scope of work and schedule regular video check-ins with photo updates.

Quote from @Katie Nolan: Here's the Oregon Landlord - Tenant Law: https://www.oregonlegislature.gov/bills_laws/ors/ors090.htmlHere's a handbook that may be easier to understand: https://oregonlawhelp.org/resources/landlord-tenant-law-oreg...If you're going to be successful, particularly in a heavily regulated state, then I recommend you study the law regularly.

Not to mention, solar panels can also be a cause of roof leaks and require regular cleaning to maintain some level of efficiency which is not great to start with while also getting worse over time.

I hear appraisals associated with ADUs regularly in southern Ca and they are typically less than 50% of hands off cost.  

If you have a real estate attorney you use regularly, they normally will do it for a low price as well.

I am not sure I've ever seen where the tax writeoffs are different for STRs than they are for MTR's or LTR's in terms of writing losses off against your regular income. 

I needed a consistent cash flow while still holding onto my regular full time job.