>>1986359As someone who has been there and done that, if you're teaching at a fairly sizeable school with quality maintenance, it's not really worth it to give that up. When you get into the small 91, 91K, or any Part 135 operation, quality of management and maintenance can ultimately be not only a liability for you, but also it could injure or kill you. The truth is, is that bare minimums for ATP hours with 25 hours dual received in a AMEL is enough to get a regional job. Unless you want to work in an obscure niche of GA like ag or firefighting, teaching to 1500 hours is just fine.
Also consider, that all your PIC for freight under part 135 by definition, does not count toward a future Part 121 upgrade. At least if you go to JSX, your PIC time there would count for Part 121 upgrade in the future. Think ahead before you hit Ameriflight, Kalitta Charters I, etc.