Hi Lisa,
Hang in there. So, you're staying with him for a while and then leaving to do Wi/Wo?
Is there a reason why you're not just picking one or the other? I know it's hard, but you might have more success if you picked one method rather than trying to combine the two.
If you stay and then leave he might feel confused...If you talk about what you're going to do i.e. Holden, first we;ll read this book, then mommy will sing you xxx fav song tuck you in and it's sleep time and then actually follow through and do it, I think you'll have more speedy results, with a less frustrated LO!
As far as the cold goes - you are the best person to evaluate that - if he's acting fine and not fussy during the day, feeling ok, etc. you can probably go ahead and do it. But if he's really uncomfortable - wait a couple more days.
But whatever you do - make a decision and stick with it. That's the best thing you can do for LO, now and later too!