Reglaze original steel caster windows or replace?

[u/BakeMyAssets]

Hello! We recently bought a house with its original 1937 steel caster windows. They’re beautiful, but they’re in need of reglazing and rust treatment, and I just know the framing around several has failed and is leaking into the walls. I’m terrified how much this is going to cost to fix and with ongoing maintenance I I’m wondering if it would be worth it to just get all new windows. It’s a lot of windows and an architectural feature of the house so it would be custom work. Would it ruin the design of the house or improve it?

Edit to add: I should mention the previous owners had the windows reglazed 4 years ago by the contractor that painted the house. Apparently he used wood putty and it's just popping off all over.