PPL > IFR > Multi > Commercial > 1500 hrs > Regional > Legacy
Oh in MSFS. 
Cessna 208 > Beechcraft 350 > Cessna CJ4
You could probably skip the turboprops and go right to the CJ4. Also the Aerosoft Bombardier CRJ700 could be a replacement or a step up from thr CJ4.
I’d give the CJ4 (WT Mod) a try and see how you do. If it’s to foreign try the turboprops.
I would not bother with stock airliners. The new Airbus 310 notwithstanding after it gets some reviews. Go with the FBW A320 for freeware, Fenix A320 or PMDG 737 for payware.