My 14 month old still eats a significant amount of "baby food" as well. Don't worry about it too much. When toddlers get sick or get more teeth (those molars hurt! ouch!), you will find that it's not unusual at all for moms to have to pull out the baby foods again. Is your son not interested in what you are eating? When we eat meals (dinner, always as a family, no TV, all seated at the table, he in his highchair), after about 11 months, we always offered our son "big people" food (cut into appropriate pieces) first. After he had eaten some of that, but was beginning to get bored with it (as in, starts playing with it moreso than eating it), we would "finish up" with some baby food puree. Our son, like I said also 14 months today, now eats roughly 2/3 "real people" food. The reason I felt compelled to answer your question is that most of my friends' babies (I know, I know-- don't compare! No really, DON'T-- it's useless!) were eating freakin' sandwiches and whole green beans months before this! Well, suffice to say my son is not a picky eater (likes brocolli florets and asparagus tips, even), but he is just not the chewer that their kids were early on. Another interesting tip to try-- our son is the greatest eater when we go out to eat. He will try anything, and wants to eat what everyone else has, without question. Try taking him out foer Mexican and see how he does with beans, avocado, and bell pepper.
As for question #2, the notion to convert my son's bed has not even crossed my mind yet. Keep him in the crib-- so much better to be safe than sorry. My son goes to a preschool program two 1/2 days a week, and when he's there he naps on a little cot (it's literally two inches off the ground), so if you want to get him used to something without sides, this might be another route to go.