Thank you, thank you for all your comments, suggestions and general nap-madness commiseration yesterday.
I ended up going with an improvised Option 4, which consisted of:
1) Letting Ike fall asleep in car, as expected, around 3:00 p.m.
2) Transferring him to the crib once we got home.
4) Stomping LOUDLY outside his door around 5:00 p.m.
5) Creeping into his room shortly after and making some sneaky background noise: sliding a laundry basket around, opening and closing the closet doors, stacking books back on a shelf.
6) Creeping back out the instant his head lifted off the mattress like a Ninja Poltergeist Housekeeper.
7) Heading downstairs to start dinner.
8) Wait for it...
9) Wait for it...
10) Oh look! Ike woke up! "All on his own," too! WINK WINK NUDGE NUDGE.
So it wasn't a very long nap (by his standards), but by changing up the waking process I sucessfully avoided the Grouchy Grouch Asshole Toddler From Hellpants mood. He was smiling when I retrieved him and only slightly clingy and whiny, and even that disappeared after a couple minutes of Transitional Cuddling.
(And you will never hear me complain about Transitional Cuddling. GIMME ALL UR CUDDLES GIANT BAYBEE.)
He ate an okay-ish dinner — a ketchup-smeared hamburger bun and all the beans he picked out of his turkey burger — then played with his brothers, had a bath and went to bed again at 8:00 p.m. without complaint.
Today I put him in the crib around 1:30 p.m. and I think — I THINK — he is actually sleeping right now, after about 45 minutes of jumping, singing and dirty filthy lies about having to use the potty. (NO YOU DON'T, YOU PINT-SIZED MACHIAVELLIAN MASTER.)
And Jason is working from home this afternoon, which means I won't have to wake him up at 3:00 p.m. to get Ezra, which means if I carry the one and divide by Pi he will get a full nap today to make up for yesterday and bank up for tomorrow, which is going to be completely obliterated for us, nap and work-wise, thanks to the 14,000 different school Halloween parties and parades I have to drag him to all afternoon.
(Okay, just two. But forgive the exaggeration, I'm really just very tired.)
EPILOGUE: NEVER MIND. He's still totally effing awake up there.