Hi, (((hugs))) a sick LO is never fun.
1) He got sick with a cold a couple of days ago and he's super clingy and cries/doesn't settle easy on his own in his crib anymore. It's really hard to get him back to sleep, we have to rock him or feed him. Obviously we don't want him more upset cuz he's sick - is it ok to resort to old ways for a bit?? Any suggestions?
Typically, I'd say to try to keep him sleeping independently as much as possible, but just offering more help. So, if he's fighting you going into the crib, hold him a bit longer til drowsy and then put him down. Or, pat/rub his back more in the crib and keep a hand on him to help him drift off. It sounds like you may be past that point though, and he obviously needs to sleep while he's ill, so if holding him is what you need to do, then you don't have much of a choice. I'd never push sleep training while a LO is ill.
2) he's been having really bad 30 min naps (he wakes up whenever I try to move him into crib) after waking up at 6;30ish in the morning. So by 2 pm he's already up from 2nd nap all cranky. Do I force a third nap within 2-3 hours since he will be super OT by his usual bed time of 6;30-7?
Is there no way you can extend the naps? Pick him up and hold him until he's in a deep sleep again? If not, then yes, I'd probably try to get another 30min nap in (maybe by bringing the other ones earlier, so you have enough time but not getting too off his normal sleep times). You could always use something like a walk in the stroller to try to get more sleep out of him as well. My DS would fall asleep in the swing until he was 1yr+, so I tended to pull it back out when he got ill.
Hope he feels better soon!