If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

I imagined that to mean that a 1920 home with no renovations would cost more to insure than one updated to 2024 specifications.Is this something that is just "known" to flippers/renovators and I am just coming across it?

Hi Emily, welcome to the BiggerPockets community!

The entity may or may not matter.

The process has been difficult and stressful and we almost gave up a few times. 

Was just going over with my wife both the increase in Occupancy revenue change and the 2023 versus 2024 Marketing spend for this location. 

You would have had to be there for at least that to save on the capital gains taxes (up to 250k). 

Quote from @Steven Diaz: Here are the prelims.   

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

Don’t forget to include the cost of the loan servicer.