I just went through this process, so I can tell you my experience.
It sounds like your FD is set for a 10 cog difference between the large
and middle chainrings, so you should probably stick with that. (e.g.
9-speed ultegra/105 fd 52-42-30)
If you want to go to a 39 middle, then I recommend you get the ultegra
10-sp fd, which is set for that jump.
I personally use the 9-spd 105 fd, with 52-42-26. I swapped out the 30
for a 26. I can use 6 of the 9 speeds in the small ring before there is
too much chain slack, but I just shift up to the middle ring. For extra
protection, I added the jump stop chain guard so the chain doesn't drop
off and miss the small ring. That is especially recommended for the
42-24 jump, which some people say works.
Shifting to the middle ring is fine as long as you shift up to the 3rd
or 4th gear in the back. If you try to shift from the lowest couple of
gears, then the pins don't catch well for me.
You might be able to adjust the deraileur, to get better than my
experience.
--Your alternative, which many people seem to do is to go with say
48-38-24 and replace all the chainrings.
I also have a deore RD with 11-34, so my lowest gear is a 26-34.
Yesterday I towed my son in a Burley on a 70-mile "metric" century with
5500 ft climbing, and the low gears helped a lot!
One other note is that when you go outside the recommended
Shimano/Campy range, then it's not dumbproof and it doesn't work 100%,
but for people who think about what gear they are in before trying to
shift, then it works great...
Toshi