LOL, Alyssa - because your post sounds a bit like mine did a few wks ago... I think so many of us get to the point where we're tearing out our hair and expending waaaaay too many brain cells trying to figure out the magical solution for our tricky LOs!
Here it is -
http://babywhispererforums.com/index.php?topic=170526.0 - just in case there's anything to glean from it.. Can't really say that we arrived at any brilliant conclusions, but sometimes it helps just to hear other people "thinking out loud", iykwim..
I think one way that you can go about figuring out how/when to set the nap/bedtime is to start by figuring out how long of a night you usually get out of H.. Is he more like a 10.5 hr-11 hr sleeper? 11.5 hr+? So approximate when you want him to wake, and therefore, when you need to get him to bed... And then from that approximate wake time, you can also set your nap - again, going with a nap length and A time that H can do. I know it's really hard when they've been all over the place and napping inconsistently, plus seeming to need different A times.. but I think you just ballpark it and go from there.
We've sort of taken to set times ourselves - give or take a bit. I almost always get L down by about 12:15-ish p.m.. mostly because that's when I'm driving home from work 5 days a wk and she falls asleep in the car.. Bedtime varies a bit from when she wakes up.. so I guess I do more of a set naptime and calculate-bedtime-from-wakeup.... I still have my "boundaries", though, of not putting her down before 6:30 p.m... and usually no later than 7:30-7:45 p.m..
I don't know if that helps any - but I DO know that it has felt much saner for ME...
L hasn't seemed to fare too badly and at least in this last wk, has seemed to be compensating for short naps with longer naps. Of course, this could all change in the blink of an eye.. but I think that's also partly toddler sleep for you. We have laid a great foundation for our LOs and tbh, I don't know if there's a ton to be gained from tweaking every little E/A/S time like we used to, ykwim? Just such a different age and stage now...
Obviously not saying to ignore all cues and become super militant (I know you wouldn't do that anyways!
) but... well.. ykwim...