{{{{{{hugs}}}}} it sounds like you've got a lot going on right now. In terms of how to approach the switch, There are basically 2 approaches to the switch:
1) keep 1st nap at the same A time every day, but gradually shorten the length of it; at the same time, move pm nap earlier (by the same amount you shorten nap 1). When nap 1 is <30 min, attempt to cut it out and just have 1 nap.
2) push morning A time later, allow your bub to sleep as long as they want in the am, then do a late pm catnap (can be a shorter A time than in the am, as you don't want them to take a full nap); eventually cut out pm catnap.
If he needs a longer A time before bed, then option #1 is generally better. If he doesn't and HATES being woken from the am nap, option #2 may be better. In both cases, you can offer an early bedtime if one/both of the naps is bad.
Whichever approach you choose - it's best to go gradually - so either cut 15 min off the am nap every 3-5 days or lengthen the am A time by 15 min every 3-5 days. It also is helpful to know about how much day sleep is "optimal" for your ds and how much A time he needs (minimum) between his last nap and bedtime - that can help you plan out the day.
In terms of independent sleeping, there are a couple of different strategies to use - gradual withdrawal and wi/wo. I'm told that spirited bubs do not like gradual withdrawal - but each bub is different, and since he does fall asleep if you hold him, he may do fine with gw (many spirited bubs don't like it because your presence in the room prevents them from falling asleep). Here's a link on the two:
http://babywhispererforums.com/index.php?topic=80750.0 Whichever way you choose, it's really important to be super consistent. Each time you pick him up and cuddle him to sleep, you've shown him that if he cries long enough and hard enough, you'll cuddle him to sleep, so he'll keep trying. When we did wi/wo with our dd (to break some APing we'd done while she was sick), it took 4 hrs the first night. But the second night was just over an hour, the 3rd was 20 min and not at all the 4th night. So it is hard, and there were lots of tears, but it did work.
If you want to develop a plan for the 2 to 1 switch and for weaning off the cuddle to sleep, we can take a look at it and help you along the way.
hth
michelle