I would recommend caution. In my younger days I would have said not to worry about the cons too much, as the pros are too fab for words!
This may sound dramatic, but I now believe some are "too far gone" to be safely removed. One such case I've personally witnessed has coloured my judgement completely. A sister with two children encouraged to leave the Borg and ministerial hubby. Once out, to be cold, she could not cope. She had no friends, no family to help, no partner, no support structure... she wasn't exactly dancing through fields of pretty flowers enjoying her new found freedom. What's more as she grew up in the Borg she seemed to lack the ability to operate in "da real world". Making friends, joining clubs, etc... etc.. was alien to her... I wont describe the fall out - but it safe to say it has not been pretty, and I often ask myself 'would she have been better off staying in?'.
Also it's important to remember that despite "coming out", some may still have hang-ups for many years to come. Once out, old fears can weigh heavy, especially on those brainwashed from childhood - this can cause depression - I've seen this too! I personally, years after leaving, suddenly started having nightmares about Armageddon - what's even more strange is that I never believed the religion growing up - so the impact on a ex-true-believer could be even greater. More trivially, I don't know about anyone else, but for years I had an uneasy feeling on Tuesday and Thursday night, almost like I should be 'doing' something?!
I suppose what I would say is, if you personally are encouraging someone out of the borg, perhaps you should consider their support partly your own responsibility once the JW rug has been yanked from under them. Consider if they have other friends, or are they social creatures capable of making new friends. Do they have hobbies!? Other non-dub family members? etc... etc...
Some are very gung-ho when it comes to this type of thing, but from my experience things don't always turn out as you might think.