Don't do it just before a long trip. Do it when you have a enough time to fiddle with jets and possible have time to order them in.
Otherwise, HECK YEAH it's worth it. My second 2002 Bonneville America has a short TORs, and a drilled airbox with no snorkel, and it runs great. Unifilter in the stock location. The previous owner put screen/scotchbright over the holes to help protect it and sorta keep the water out. I rode it through BC in a torrential downpour and hail last July and it performed flawlessly. I haven't confirmed the jetting myself but the paperwork seems to indicate 135 mains.