#1 - For the chigger bites, clear nail polish really does work. I've used it before, and it's the only thing I've found that fixes the problem.
#2 - I moved both my boys to a twin bed around the age of 2. With both boys, we made a big deal about the big boy bedding and sheets and totally did a room make over to a more grown up theme than the nursery. For my first, it was because we were pregnant with #2, and I didn't want him to feel as if he was losing his bed to the baby, so we wanted plenty of time for him to "forget" about using the crib before it was set up for the baby. As for my second child, he was climbing out of his crib. (He'd jump on the mattress and fling himself over the edge like a pole vaulter - I can't believe he didn't break his neck!) I didn't do a toddler bed because I didn't want to invest the money in a bed and bedding he would only use a short while. (Our crib did not convert to a toddler bed.) So, we got a twin bed, pushed it up against the wall and put a bed rail on the outside of it. I also had a step stool at the foot of the bed so they could get up in it. Both of my boys did really well with the transition. The first couple nights were tough and we had to constantly put them back to bed and reiterate they are not to get out. After a couple nights, it wasn't a problem, and they both adjusted well. In your case, at only 16 months, if your son is not trying to get out of the crib, I would wait. That still seems like a young age to me, but I have known people who have been able to make it work. If your son is happy in his crib, I wouldn't push the issue just yet. However, if he's trying to climb out, then it is probably time to make a change.