Really don’t over think, just get some good diverse experience in the time-building phase.
Here was my path,
PVT - Part 61 school
IR-Comm Multi - Part 141 school
CFI, CFII, MEI - Part 141 school
Right seat - 421
Some charter flying in a 310R
Interned at a Major - (got about 15 hours of sim time in the MD-80 and sat in on the MD-80 systems course)
Instructed - Part 61 school
Part-time charter flying in BE-58
Currently Right seat CRJ
About to be left seat CRJ
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