These regions are where I typically suggest looking if investors main goals are maximizing Cash flow/Cap rate/ COC return

If you are looking for ways to track/calculate principal and interest payments, you can use loan amortization excel template, plug in the principal amount, loan date, interest rate, and the number of years to pay and it will show you the monthly breakdown/details you need to track the loan.

We are fully booked for high season (Dec-March) through 2026.I know this is not the typical investment, so totally appreciate any advice anyone may offer. private money will most likely be at a rate of 50% greater tahn the primary.

Oregon were i am at is bad with this as well on the resi side.. but on Commercial there is no squatting those laws that resi tenants have do not exist for Commercial you post a 3 day notice and then you can legally enter change the locks kick whoever is in out.. that includes your commercial tenant that is not paying. 

Interest rates will be 7.5 - 9%~HELOCs on an investment property typically come at a higher interest rate (13-15%~).

My current agent advised me not to "rock the boat" with the policies I currently have because they are all older and would "go up significantly" if I changed anything.

Those interest rates are never coming back.

LOL I am kidding but insurance carriers are pulling out of CA at alarming rates.

They run a tight ship on screening and have a almost non-existent eviction rate.

Westchester 2-4 unit properties listed from January - May:2022: 2332023: 177 (Lower inventory likely due to the market adjusting to 6+% interest rates)2024: 274Lastly, since you're looking to acquire something with more favorable #s, you may want to begin your search with the "ugly" deals that have been on the market longer.