My transactions at namespro have been smooth and without any issue. If anything just ask them how many names their bulk-transfer form supports - to see if it would support 2000 in one shot, although I don't see why it shouldn't.
It's pretty much the user that needs to complete the transfer process - you'll be at CIRA clicking "accept" 2000 times which will probably be cumbersum, even doing 20 names can be slow - you need to wait a little bit between clicks, eitherwise you'll get some error "a request is already being processed" or something like that. You only have something like 7 days to do it, not sure if Cira sends you a reminder if you miss any though...
It's pretty much the user that needs to complete the transfer process - you'll be at CIRA clicking "accept" 2000 times which will probably be cumbersum, even doing 20 names can be slow - you need to wait a little bit between clicks, eitherwise you'll get some error "a request is already being processed" or something like that. You only have something like 7 days to do it, not sure if Cira sends you a reminder if you miss any though...