It's basically a legal 2-unit that can cashflow $900/month.

Or really they were ALL pre foreclosures when it was legal to do this in OR and WA laws changed in 08.

Reflecting on the last 20+ yrs, when we could cash flow immediately with low cost sfr, had we gone with the higher priced properties and significantly lower cash flow, more debt, we could not have achieved IRRs even close to what the lower end product has delivered, nor paid off the investments. 

Yes, I have general expenses that are not attributable to a single property, like legal and accounting and home offices like you mentioned.

That's before you pay any debt service.To answer your question: No, it's generally not a good idea to lose a bunch of money every month.

LLC offers better legal protection.3) Setting up in states that allow your identity to be hid is also overblown.

Additionally, since my parents are nearing the retirement age, I'd like to prioritize low-debt, high-cashflow deals.

I did serve a 5 day when they were late for rent and can legally nullify the lease and do a 14-day notice in Wisconsin and escalate for an eviction if it happens again. 

Waiting until you get a deal under contract to then see if you can put together the debt and equity is a recipe for disaster.

All existing STRs with 2 days rented in the last year will be granted legal non-conforming status.