Worst case TYPE rating
You still need a type rating to fly TP's
But what he's saying is ... He'd prefer not to have to pay for it with his own money i.e. SSTR
I think your plan is a good one, it's the same as I am doing;
PPL & Night (in Florida)
ATPL GS while Hour Building
CPL & FI
Find an FI job
ME
ME-IR
MCC
Apply to Airlines (TP and Jet) with 1,000hrs+ on my log book.
Although I am looking into converting the JAA CPL to FAA CPL and getting an FAA ME-IR and then applying to Ops in the UK operating 'N' reg AC.
Good luck.