There is risk with this approach that the tenant can have short residence or leave in Nov to January.  

The desire to replace W2 income is a mistake many make when approaching real estate as an investment. 

If there is any kind of damage to the house because of a natural cause if you approach the insurance company without a landlord's insurance they will outright deny your claim.If you have a mortgage the bank will insist that you have landlord insuranceTenant has renter's insurance.

Keep in mind local zoning laws and market conditions in Portland versus Salem—Portland might offer higher rents but stricter regulations, while Salem could provide better cash flow opportunities.Your design approach has proven successful, so continue focusing on appealing upgrades like kitchens and bathrooms, but prioritize cost-effective and durable materials for rentals.

I concur on the Section 8 approach  and don't forget the complete background check.Stop the bleeding first.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Hey Jason - if it's a 1-4 unit, you would need to value it based off the sales comp approach (assuming the buyer is using debt financing).

One of the best resources I’ve spotted for honest property management feedback-beyond scanning Google-is checking local Facebook investor groups and seeing who people recommend.Anyway, Ethan, since you’ve done a bunch of data crunching: have you or anyone else revisited these numbers more recently, and if so, how have shifting mortgage rates or local employment trends changed your approach?

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

So you could also approach it from that angle.