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.

How are you approaching the process of lining up buyers for each property?

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.

The guy is genuine in his approach and really does help people get across the goal line.

That would seem to mean he has a problem with his 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?

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.

While the traditional approach involves buying a multi family property, living in one unit and renting out the other - with rising prices and interest rates; others have considered renting out bedrooms as unit spaces. 

Investing does need to be approached more like a business than just a simple stock trade.

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.