Dear Davve
I hve more than 2000 on 737 900ER, i flew classic only on the sim, from my point of view if you can manage a good flight ( and you should after 500 ) in the classic you can definitely have an easy upgarde on the NG, you'll have to deal with Smart Landing Feature, FMC software 10.8 or later , different cross scan but mainly features you can learn from the book, manual handling will be different, expecially during FD ILS , visual pattern and flare tecnique but all things you can deal with a small and simple line training...
The real problem is that if i can not find another decent job with more 2000 hours on NG how could you ?
The fact that you have 500 on CL will be the first reason they will use to ask you to pay the line training again !!
For most of the airlines you will be below minimun requirements, 500NG was good maybe 3 years ago but now , if look around, they ask for 1500 and 60% of them dont even reply to you as they have plenty of applicants with more than 1500... only the most reputablesairlines will answer you telling that you are in the Pool.... ( i'm swimming more than one year right now ) and the only way to move on will be to put the money on the table again with a crapy 5 planes airline that makes more money from cadet training than passenger transport !!
This is maybe the reason eaglejet, is selling line training + employment, becouse everibody already knows that with 500 you don't go anywhere... and even after that contract you will have 50% chance to go back home and start selling cars after being repleased by the new fresh cadet ( withc isn't so bad compared to the nightmare i'm leaving now )
Sorry for being so cruel... i just hate them so much ...