I have had two 'velcro babis' as I call them, and yes, for a few of the early years it is incredibly difficult and frustrating but they do get better.
DD2 (first velcro baby) now is my most confident. se has changed schools twice in the past 2yrs and not been phased and soon made good friends, and also started scouts (her choice), again without nerves, and now goes camping ec without a backward glance. doesn't even want me to stay and wave her off, just drop and go.
DS2, (my now velcro baby) is now 5 and still a little glued. I am not sure tho if that isn't just because he is the youngest of 5 and 'my baby' (yes, I don't help), but also he had been in hospital a fair amount as he has a bowel prob. (mind you, may not be the only reason as DD2 and DD3 both spent more time in hospital as they have immune probs).
anyway....DS2 is coming round. he is going to start beavers at easter with DS1, and altho he finds going to school hard (well, saying goodbye is more the prob), he is always ok once there.
My view is, they are tiny for such a short time, and altho is is hard, and may drive you near tears at times (it did me!), if you can go with it then it wil ultimately pay off in a confident happy child who doesn't feel scared of their feelings as they were always taken seriously while younger. AND, they will always know that if they do have a wobble, mummy is always there to give a much need huge hug and put them back on the path again.