I'm currently a CFI/CFII working at a flight school averaging 90 hours a month and taking online college classes. My times are 1023/100. My goal is to work for some airline . ( Regional Major, doesn't matter )

The only problem is, I have to wait five years for the ATP age. (23).

My plan is to go fly cargo, (Ameriflight or some other) until I reach the ripe age of 23, then apply to a regional, build jet time, and go to a major.
Does this sound like a plan?

Also: I have 3 busted checkrides. ( Busted the CFI oral 3 times. I should have prepared better). Will this matter in five years or in 5,000 hours having passed many 135 checks?

Those plans always sound nice on paper. Be prepared for many changes and bumps in the road. It does, however, sound like you're on the right track.

There doesn't appear to be anything wrong with your plan. Ameriflight has good upgrade times..just some weird bases. Does Ameriflight make their pilots have ATPs to upgrade on a turboprop?

As far as the check ride failure..I've never heard of anyone fail a single oral 3 times. One thing you have going for you is the CFI check ride is arguably the toughest of them all. But if you do well in 135 training, and most importantly, you're honest on job apps about the failures, you should be fine.

I was in a rush to get the CFI. I busted the oral, tried to take it 2 days later, failed, then tried again. I will never study for another ride like I did for the CFI.

First person ive heard in a long while fail an oral...let alone 3 times in a row!

I suppose some things you will have going for you on that one are:
1: Time...it will be 5+ years old by the time you interview
2: You were young..tell them you were naive, make something up that shows that you were young and dumb but have learned and are now new and improved.
3: People fail the CFI a lot..the bad news...its usually the ride.

As others have said, dont forget to live...you will undoubtedly meet the mins by the time you are 23 so have fun, go to school, drink beer, spend time with strange women etc etc. Most importantly..DONT GET ARRESTED! Its harder than it looks when you are young and dumb and out there in the big drinking world.

Have goals..be careful with plans. A lot can change between now and the next five years, and it will. You may meet a girl and get married and that will change your whole outlook on where you can and cant work geographically and your money and time constraints. Just be happy that you have so much flight time..at least you wont be struggling to meet the mins for the ATP at 23. If I were you, I would start networking my way into right seat of something turbine at or near your field.

Really? What's the reason people bust the oral?

OR...

Finish your degree, ASAP, join a Guard Unit, go through Military Flight School, where they will teach you how to NOT bust an oral or a checkride. By the time you get done, you should be about 23, get your ATP. The age 65 retirements will be in full blast in 5 years, so the Majors should be hiring, you'll be a "Military Pilot" with an ATP and a lot of time, you should get hired somewhere.

Worked for me, 1981-85.

When they open their mouth, stupid things come out, and that's before the Oral even starts...

Not knowing the material..either that or the examiner had outrageous expectations.

Best idea by far. This would be a brilliant option.

I dont know, you tell me the reasons you busted the oral.

I worded that wrong. Which is a common reason people bust the CFI ride? The Oral or Flight?