Question:
So I had completed my PPL a year prior and after leaving the military decided to go to a prominent accelerated flight school to get my ratings quickly and boom 4 busts in record time: IR oral, IR flight retest, CMEL(initial)x 2. I decided to leave this training establishment after these bust due to finances because there was a lot of delays with weather, and the busts didn't help either. I have been working maintenance side for the past 1.5 to 2 years (I am also A&P ).

All my checkrides have been with the same examiner including my PPL which I passed first time. I ended up having to get another examiner for my final recheck for commercial multi. I didn't have much say in DPE choice, the school just set you up how they wanted to and availability in the area. I could go into details on all these busts but that's not why I am here. I have learned from them despite how unfortunate. I am just seeking some advice on if it makes sense to even try to fly for a living. Would getting my ASEL add on, CFI, CF-II without failure make me more marketable? or would it make more sense to just build some time and try to get on right seat with a Part 135 operator or something like that? I don't have an issue with the airlines, but the end goal for me is more like being the captain on a G-VI or Global flying around the world. Or do I need to give up, fly for fun and just be the best mechanic I can be?