note* "Lunatic" wrasse is just my own personal "joking" name for them - just in case you don't realise

- and if you have every seen one (especially diving) you'll know why!
I say the wrasse coz it is lively and bright colours and a really cool fish and about the only thing I can think of that will go with a clown trigger with any chance of sucess......
The blue devil damsels for a bit of life, colour, and they will pick up any little scraps of food (which I am guessing will be plentiful).
A 2" hole will take a 1.5" bulkhead which should easily take 1000 gals/hr - probably nearer to 1200..... not familiar with that pump - what flow rate will it produce at your given head? I'd personally aim at something that will produce 1200 gals or so, at the head you need ..... you can always tap it back a bit.....
Do you intend on having sand? Dunno how a clown trigger will behave with a DSB? It wold cetianly help manage nitrates etc...... but he might just blow it all up for fun.....
Sounds like a great tank - I'm sitting in from of my 8x2x2 tank now thinking!
As far as the skimmer - just make sure you can fit it in whereever you intend to put it, and then get the biggest one you can afford!
This is gonna be a cool tank!