If it ain't broke should I or should I not fix it?

[Val J.]

I have a property that was built in 1939 that I purchased nearly 2 years ago. I'm wanting to put new windows in the house and I would like advice from my fellow BPers. First, I'd like to know if you were in my shoes would you put new windows or just keep what's there (original windows)? Second, I've contacted a contractor who has given me a bid of $5500 for double pane single hung windows.  This contractor is asking for 1/2 down and the balance after the job. The payment would be made out to him as well and not directly to whoever his window supplier is.

I got another quote from a Universal Windows who can also do the job for about $6800. With this company I would be allowed to pay a % down & the rest in payments

Either choice would of course cut into the budget. This is my first major purchase for this property so I would like input on the best way to proceed.   Tell me how you would handle this.