Yes, it would be worth it if it put him in a position to get benefits/significant raise. Yes, it seems like a pain in the short run, but two years isn't too terribly long to wait.
Whatever's cheapest for cooking (unless a recipe gives a good reason for going with a specific one, like if I'm making French onion soup); red onions if being eaten raw.
Like other people, we always do reading, writing, and math. I try to plan read-alouds and hands-on projects so that we hit on science, history, music, art, etc. regularly.
30-45 minutes of "serious" work (reading, math, handwriting); as long as they're interested for the "extra" stuff, like history, art, music, science (can be surprisingly long sometimes).
most recent purchases: office supplies, memory cards, birthday presents (love that you can ship them right to the recipient at no extra cost), used curriculum.
Okay, I feel better about one of my kids who likes listening to classical music but HATES the composers bios (we've been doing composer studies). If they're focusing more on the actual music at the college level, that's what I;m going to let him do!
More often than no, the t-shirt under the sleeveless looks awkward. By all means, use a shawl or wear a sleeved shirt over the tank top if you want to cover your shoulders--that looks so much better.
I use smugmug--unlimited photos, and it makes it easy to share pictures of dc with family members. We have the plan a level up from the basic that also lets you upload/share unlimited video. i find it worth the money, but i can see how others would prefer something free or cheaper.
I agree that it's normal at this age. I just clarify and say "actually, sweetie, we did that last week. yesterday, we ...." At some point, they figure it out.
I'd also check thrift stores. My local St. Vincent de Paul stores have pretty reasonable prices for large bags of them (~$5). I got a great deal on them at a rummage sale once--$2 for a big trash bag full.