Dragonite question

You may take #1 to level 30, it's almost there. I would power up #2 with no regrets. May charge TM #4 to get another Outrage, but you may not really need it and might as well wait 3-4 months until Gen 3 introduces new moves. I wouldn't invest in #3 and 5

N.2 to level 33

I prefer at least one dragonite for each useful moveset and at least L30. Therefore, I keep the following:
DB/DC
DB/HU
DT/OR
DT/HU
DT/DP

Bring DB/DC to the 3000 club. Likewise with DT/O.

I like DB/H but DT/H doesnt feel right. O is the best pairing with DT.

Power #2 as much as you can. DT/O is a righteously good moveset, and the IVs are top shelf. I have the same exact mon (14/14/15 with DT/O), and have him powered to level 35.5. The ultimate generalist. As long as I avoid ice, he's really useful.

Also, #4 is also good as an air attacker (there aren't that many good ones), strong against Machamp and Grass and Bug mon. Or you could TM to get another DT/O - for my second Dragonite (caught wild at level 30, decent stats, but DT/HB, CTM'd to DT/O) I would have been cool with hurricane, but got luckier and got Outrage.

The good (sort of) thing about Dragonite is that as a generalist, you don't need too many of him. If you want to take out Zapdos, best team is 6 golems with all rock moves, so having 3 or 4 golems is better than using Dragonites. 4 Dragonites don't get you that much in the raid meta game, as they aren't listed as a supreme counter for any raid boss, but are listed as good for many. One or two to fill in gaps are good, but you don't want to be attacking anything with 4 Dragonites on your team; it means you have too many holes (or are making do with what you have, which isn't terrible.) Further, I can't imagine that any potential raid boss will have Dragonite as a supreme counter, as Dragon is only strong against Dragon. So if you go up against a SW/HB or SW/H Dragonite raid boss (doesn't exist yet), then a DT/O would be good, but attacking with ice would be even better, so why not do that? Articuno, Lapras, Jynx, Cloyster, and more from gen3 (Walrein, Regice), and gen4 (Mamoswine and probably more) all look like better choices.