Normally stereotyping refers to ignoring the particulars pertaining to an individual in favor of making judgements based on generalities.
I fail to see how this is an example of that. We don’t really know much about the OP other than he is 29 years old, may have very good stick and rudder skills (per self report), has been sentenced to some jail time, and failed the checkride twice.
You asked what of his background might indicate he would have a problem finding a job as a professional pilot?
I responded that the jail time and failing twice were two such items.
You then said that was a stupid thought.
In this last post it strikes me we agree that the jail time is likely to create some issues with finding a job.
About 10% of people might be expected to fail the checkride twice, so while not terribly rare it is less common and those results suggest the OP is in the bottom decile of CFI teaching ability.
So based on those facts and agreement, I honestly don’t see why such an opinion or evaluation is viewed as being so terribly offensive to other posters on an aviation board. It is unclear why a comment about the OP would be perceived as applying to more than the OP in the first place. Unless the majority or a substantial fraction of pilots here have been sentenced to jail time and failed their CFI checkrides two of more times. But I don’t believe that is the case.
But we really don’t know much about the OP and he could provide more information if he desires more accurate evaluation.