This psychological trap causes us to stick with a plan even if it no longer serves us and the costs clearly outweigh the benefits."

I’m seeking advice from any investors who have dealt with the pain of owning a co-op in NYC.

Having it in both FL (my domicile) and CT (property location), created double the work and fees in both states.From what I can tell this isn't the right entity structure anyway, so I can imagine it was a pain with many extra costs! 

Those may help craft a plan for how to minimize the pain. 

Out of curiosity, anyone care to share their biggest pain points, gripes, or frustrations with building financial models?

You can install water meters (not city ones) that can monitor the water usage but the record keeping and calculations can be a pain.

It ties into your great grandfather’s troubles during the 1932 depression; your grand parents ability to purchase a home in 1953 for $100 down with a VA loan, and your own psychological well being at having to have a percentage of your income going to pay debt each month.However, unless debt is so debilitating to you that it keeps you up at night and inhibits your ability to make rational decisions, the decision to pay off debt early is merely a function of numbers.  

Yep it’s a pain in the butt but well worth it.

Overpriced and pain to deal with, especially with a large portfolio of properties.

Lender 2 requires 6 months reserves. they want the borrower to document any large deposits and they want mortgage statements on any investment properties listed on the 1003.The point is different lenders do different things and it's important to not generalize as a broker, but interview the borrower, find their pain points and marry them with a lender that will minimize those pain points for a successful close.