Some people have been very successful switching, others have more trouble, as the act of vaping is more similar to smoking than dipping. You shouldn't experience any physical withdrawal, as the nicotine delivery from vaping is very adequate.

Once you adjust to vaping instead of dipping, you shouldn't have too much trouble between breaks. Compared to smoking, the addiction changes quite a bit and is less nagging, less urgent. You might be able to employ a "stealth vape", a small, low powered device that won't produce clouds, but with a fairly strong juice will give you a hit in a pinch.

General tips in no particular order...

Don't cheap out on your initial equipment. A good quality device with a pleasant juice makes the process much easier. Do a bit of research, find a compromise between price and quality. I highly recommend a variable wattage device, and the Kanger Subtanks are very nice for the atomizer.

Don't over-estimate your nicotine requirements. A common mistake people make (and I made a year ago when I switched) is to go for the strongest dose of nicotine available. It's not needed. Starting with an average dose, perhaps 9-12mg/ml is usually plenty.

Don't try to limit how much you vape when not at work or on breaks. You'll probably find you spend your time chain vaping for awhile, and that's OK. It'll settle down as you adjust to it, and if you want to, you'll find yourself able to lower your dose periodically.

Opinions will vary on this one, but I think it's most effective to try to switch entirely, rather than to use more than one source of nicotine. The first day or two can be difficult just because of the change in habit, but once you adjust to it, you're home free. I've known people who tried to taper off smoking while vaping, and usually they just ended up supplementing their smoking with the vape when in places where they couldn't smoke. A clean break eliminates that struggle, at the cost of a day or two of drastic adjustment.

If anything above sparks more questions, fire away. :)