I'm sorry. I hate to bring bad news but you are really behind the 8-ball with your history. I talked with two hiring recruiters, one at my airline and one at another top five regional I know. I did not share your age, but just the information you provided. You are not disqualified from part 121 flying by the federal background check, but you are right on the edge. If the 2000 conviction was a felony, you'd be out 10 years from that date, no question.

However, both said it would be unlikely your app would be pulled for review from the online systems. The reason is when they apply filters to the system to pull selected apps, they usually say "no convictions". Therefor you will need a very very strong recommendation to even surface your app because the recruiter is going to have to pull it by name. Then let's say you get to the interview where you will have to admit to the other arrests (the apps only ask for convictions). Your interview will probably be politely over there. The reason is companies won't spend the money on a background check on you. This is usually done while you are in training (why - they don't want to spend the money on people who don't show for training). They definitely won't let you start training for fear you won't pass. Lastly they just don't need to. There are too many pilots available that don't have your situation.

I strongly agree with what CalCapt said: persistance and a great attitude in this business will get you a long way. However, in your case I'm not sure persistance will be enough. I agree with others, especially at your age. I was hoping you could just hold off a few years and pursue the dream later in life. But at 44 I really think you are better off focusing on a corporate pilot or other position than hold hope for a part 121 job.

I wish I had better news. Maybe others here have different information. Good luck to you.