SD3DOG, I'm not a legacy guy but here is my 2cents. I was in your spot once. I chose upgrade on the shorty over a job on a CRJ. I did this because the majors were hiring like mad and I needed the TPIC to be a candidate. The shorts was the quickest route to that. With everyone hiring full swing it will become more and more a sellers market. On top of that not as many people are applying since the contracts got gutted. This will make it a sellers market much more quickly. I had a friend get hired at the majors (in a sellers market) with 2700 total and 700PIC on the shorts. He was also fairly young, and a flight engineer on a DC10 for 9 months (read, I can pass 121 training). I think those things along with his GPA, etc helped him. I didn't get to the majors before 911 (missed out on 6months of that FE time
) but I still think the TPIC first is the best, quickest course, especially in a sellers market. So did all the legacy guys I asked at the time. Don't worry about schedules and the rest. You can do anything for a year or two.
Then go get the 121 job and wait.
Best of luck, keep the ugly side... uhh, scratch that, keep the wheels facing the dirt.