Good for you Yankee! Since it's your first scanner, you might find there to be a bit of a learning curve in programming. But once you spend some time with it and get the hang of it, it'll be easy. That said, I had a PRO-92 then a PRO-106, which both had very similar programming software... and both of those apps were very similar to EZ Scan which will come with your 1088, so the learning curve was pretty flat.
You might want to download EZ Scan from the Whistler website and play around with it before your new toy arrives. Also, I've found that the best way to learn programming of a new scanner is to program it by hand first and learn its menus... not large systems, of course, but start with a few conventional channels and maybe a few talkgroups on a local trunked system. Once you get the hang of programming by hand, then the software should be easier, and you'll have the knowledge to make changes on the fly if you're not near your PC.
Hope that helps...