[huherto]

> 1.) Does there ever come a point where it just isn't worth it to continue trying to be a software engineer who can get into top-tier companies / projects?

Don't just look at the top-tier companies / projects. There are many projects/companies where you can learn, grow and contribute.

> 2.) How can I find some positive reinforcement in interviewing / interview prep even if I constantly get rejected? I do perform post mortems on every interview in order to find areas to improve.

Are you getting a positive reinforcement when you are doing software engineering ? That is the key question. If you do, you can have a very satisfying career. Even if you don't work at google.