Hi Courtney,
I find that with my ds, if he has one longer nap a day (which usually ends up being the mid-afternoon one), and two shorter ones, he's able to function without being very cranky. He has for the last two days been having decent naps both in the morning and the afternoon and a short cap nap later in the afternoon.
If my timing doesn't work out during the day and he's tired, I put him to bed early, around 6pm. I usually try to hold him off until 6:30. If he happens to wake up early, I give him his soother and hold him off until 7am if possible.
A babies natural sleep biorhythm is to wake up at 2am and 5am. They are able to sleep through the 2am awakening first. If your lo is not usually up at this time, you should be able to get him back to sleep. You might notice that his nightime sleep patterns change a bit as his daytime sleep is organizing itself.
I found that the more I tried to manipulate his daytime sleep, the more he would wake up at night. I'm happy to say that after a few rough months of short napping and crankiness, the waiting is finally paying off.
I'd say find the right balance of how involved you want to be in helping him to nap longer, while keeping your sanity.
Good luck! Heidi