Drove 8 hours to inspect before closing, all looked good.

Example: November 2023 sold for 500kListed under foreclosure for 260k now.Photos don't show any updates or signs of any rehab being started.My first guess it these were bought as rehabs without inspection and people found severe structural issues that they cant afford to remedy, which is common with the amount of water around us on Long Island.What other assumptions or conclusions would you draw from seeing listing like this one?

We have called an exterminator to come out and do an inspection. 

Having a team in place that understands the laws, inspections, etc. was crucial for me.

And calculators are only as accurate as your inputs...Did you inspect these places?

Have quarterly pest inspections. 

For example, moving out a tenant includes about 30 steps like pulling their file, emailing them the move-out instructions, changing the lease in my software to "Active - Notice Given", stopping recurring charges and payments, prorating last month's rent, scheduling the pre-inspection, etc.

Insurance and the structural inspection and associated repairs resulting from the fallen seaside condos has resulted in huge HOA cost increases.  

The 2 year certifications require dust swab samples from multiple areas (windows, window sills, floors) of each room (not basements) and the exterior must also pass visual inspection. 

Clues    https://www.boston.gov/departments/inspectional-services/short-term-rentals#:~:text=Boston's%20Short%2DTerm%20Rental%20(STR,%2C%20and%20three%2Dfamily%20buildings.