One number I heard is 2 per 90 days but you can always call Microsoft if it gives you an error when you try to do it more.
Another option is a tool to
back up your tokens and then supposedly you just reapply them.
Won't help your custom built but for anyone finding this: Laptops are usually preactivated so, I believe, even after a reinstall you don't need to go online or call (someone correct me if they know different). There are also KMS keys that corporations use to activate many computers which also would not be subject to directly contacting Microsoft.