Per your request in the video, here are my suggestions:
1) Budget. Obviously a major consideration... Interestingly, low mileage TJs in nice condition are holding their value. For me that was one reason to also start looking at JKs
2) Location. Looking for a TJ in a rust belt state is much different than in the South or West. Rotted out frames are a common theme here. A vehicle from another region of the county commands a premium (see #1). Future vehicle health should also be considered here as well.
3) Usage. Be honest about this with yourself. Daily driver or additional vehicle? On road only? Off road only? Summer only? You get the point. Don't leave out passenger consideration too... The JK I purchased is much easier for my wife to get in and out of vs. TJ (or even the new Bronco we had).
4) Future plans. This is closely related to #3. Keep it stock, upgrade it, or find one with with modifications already completed? Understanding of lift, tire size, gearing and how they relate since this is a common upgrade.
5) Research. Knowledge of the features and content through the years as well as on the various trim levels. I can't tell you how many Rubicons I see driving around in my area. I'm making an assumption here but would bet most of the drivers don't understand when, why, and how to use the lockers. Honestly they probably don't even care... This also includes common issues throughout the years which you said you would be covering.
I ended up with a 2dr JK Sahara 75th anniversary edition. It pretty much hit the sweet spot for me. Happy to share any details about my search.
Looking forward to your upcoming videos in this series.