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.

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.

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

This cushions potential value drops.Syndicator vetting: Only partner with syndicators who have a strong track record in different market conditions.Market and asset class knowledge: Understand market cycles and the specific real estate types (multifamily, industrial, etc.) you're investing in.Avoid chasing trends: Just because a market or asset is “hot” doesn’t mean it’s solid.You’re right that this approach doesn’t cap your upside, quality diversification can still generate huge returns while managing risk.Best regards,Drago

I really wanted to try Wholesaling and thought his approach to Lease Options was interesting and expected a sort of 1 on 1 or Small Group type of course but there was nothing like that.

I know my first question if someone was trying to approach me is to ask them for credentials, experience, etc...

I'm a beginner as well, but have been reading this site enough to see the recommended (over and over) approach is to leverage your presumably un-tied-down youth to move every 2 years, each time using 3.5% down payments to buy multifamily buildings / house hacks. 

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.

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?

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.