Will Quicken Deluxe 2000 run under Windows 10?
No. Even Quicken 2004 won’t run on Win 10.
Was going to suggest running it under Wine on Linux (in a Win 10 VirtualBox Linux VM) but the AppDb does not give high compatibility marks for Quicken 2000.
You might want to take a look at GNU Cash, https://www.gnucash.org/.
I was very close to moving to it two years ago but it does not have the balance forecast calendar function that I use a lot. I ended up buying Quicken 2017 to run on Win10.
Unfortunately Quicken has moved to a subscription based model with it’s current (2018) releases. So if you use online or some other advanced features they may expire when your subscription expires.
Another alternative is to use an online service such as Inuit’s Mint. (BTW Quicken is no longer part of Intuit)
HomeBank is an easy accounting