In the interest of having a little fun I want to see what you all would do in my situation, and then I'll let you in on what I've decided to do. I've consolidated and sold off some of my gear and I've just scored a nice commission cheque - I have about $2-2.5K in "mad money" set aside to spend on myself - and if there's any left over I'll certainly be doing something for the fiancee.
Here's the equipment I'm left with:
2 x 30D
17-40 F/4 L
EF-S 17-55 F/2.8 IS
70-200 F/2.8 IS L
100 F/2.8 Macro
I ran the gaumet of what camera equipment I wanted to buy - I thought about new bodies - 50D, 5DMKI, 5DMKII. I've been over getting new glass - 16-35 MKII, 24-70 L, 24/35/50/85L, etc. I've also entertained ideas of indulging in my other passion which is guitar. One thing I'm not interested in is adding any more EF-S lenses to my bag.
FWIW - for pay I'm shooting weddings, stock, and taking on some commercial work. For personal shooting I'm into landscapes, urban decay, abstracts, etc.
If you had my equipment, my mad money to spend, and your shooting interests, what would YOU do? Again, this is just for fun - I'm not really looking for advice on what to buy.