Thanks everyone for the help! And yes, I meant EXP status (not Diamond). I don't need to worry about retaining EXP as I fly the RJ's 99% of the time and have 40 for the year so far. I don't think I'd ever make it on the miles. I got lucky having 101 segments last year and was shocked to see EXP print on the boarding pass one day
Anyway, I got bumped tonight, so I'm definitely buying my ticket now with the $250 voucher - yeah! My concern now is for the other ticket. I could use the 18750 miles and have us both in coach - I would not want to be upg to 1st by myself or go ahead buy the 2nd ticket and use 4 of my 8 EXP upgrades to have us in 1st class since I don't know how else I'd use the free upgrades.