Quote from @Helena Wheeler: I'm in MS looking to buy and hold properties.

Do you include specific clauses in each of your subject to deals spelling out exactly how insurance on the property will be handled?

I’m based in Portland, Oregon, where residential investing seems challenging due to landlord-unfriendly policies and negative cash flow on higher-quality properties.

I’d love to learn more about how you operate in multiple markets and what strategies you’ve found most effective for managing properties remotely.Looking forward to staying connected!

For example the BRRRR strategy worked with many properties 10 years ago when the average mortgage was cheaper than the average rent.

My next goal is to invest in a multi family property with a partner.Welcome to BP!

They often have access to off-market properties which gives you less competition.

Quote from @Gregory Wilson:As for the second, there are only about 20 monetary numbers to be entered in Turbo Tax on a single unit rental property 1065 so it always seems to me that the $3500 would be better spent elsewhere.

Would living in the same property as my tenants have any downsides?

All is not lost, if you can find a seller of the apartments who is alos willing to finance the purchase for you;  Or look for a private/hard money lender.