SkyWest use to require, and may still - I haven't looked in years, 2500tt with a 1000 multi turbine in a crew environment. And the crew environment didn't have to be 121. I think the new ATP regs added a requirement as well.
Upgrade has been awarded to those in new hire class before. IAH with the Brasilia back around 2005?
As far as now. Just looking a the DTW bids it'll be at or under 2 1/2 years.