$2500 for a tranny job? Dude, it sounds like they think you are rich or the tranny guys like to get down and dirty with blonde geeky looking guys!
That is a freaking rip off even at this day and age!
They might have the think apart but didn't they have a free estimate, etc?
If you act like you are backing out they might realize you are not going to bend over without having any KY applied so they might drop the price.
I would always pull a 'puppy' face and act like my entire world just crashed on me and I was about the cry and I would mumble something like "I don't have much money so I don't think I can get it fixed...sobb"
That sometimes worked...

Well, depending on the make/model, year, mileage try to figure out how much it is worth then compare the repair charges to that number if the repair cost is more than 50% of the car's value, I wouldn't spend it, if it is between 35% and 49%, it may be worth it and up to you, etc...

PS. Btw, I have a used bicycle for sale!