So far I have done a lot of reading and lurking so I hope my first post will be helpful.
For background, I started with CB radios almost 25 years ago. Went on to get my ham license and have had that for over two decades (since 1993).
Just about any CB setup will work if you can see the other vehicle on the trail. Better antenna systems will get you more range up to a point. Once you go so far, better range comes with more powerful equipment and frequencies (like ham radio bands)
Think of an antenna system as three parts. The feedline (usually coax cable), The radiator (antenna looking part), and the counterpoise (also called a ground plane).
The feedline is pretty simple, typically standard RG58 or heavy duty RG8. RG58 is much more flexible so it works better if you are snaking it through small cracks to make it look pretty but RG8 can handle much more power. For most folks running legal power, RG58 works fine.
The radiator is what most folks think of as the antenna since it's the part you see. Most are either fiberglass, metal, or plastic. Firestik antennas are wire wound fiberglass poles with heat shrink tubing sealing it up. They are everywhere since they are popular with truckers. They are stiff since they are fiberglass so they are more likely to get broken off on the trail. Adding the spring to the bottom can help with this. A lot of Firestik antennas have a screw in the top to help with antenna tuning. Metal is another popular material for radiators, They can be longer since the metal can support itself better but a tall antenna scrapes and bangs on EVERYTHING! Proper tuning of a metal antenna is simple (you cut some off!) but that scares a lot of folks from doing that. Some of the knock off Firestik clone antennas will use a plastic rod instead of fiberglass. They work pretty similarly.
The easiest way to describe the counterpoise is the other half of the radiator. Just like the old every action has an equal and opposite reaction line, an antenna radiator has to have something to work against. This is the counterpoise. When you mount an antenna, the perfect spot is in the middle of the vehicle at it's highest point. This would maximize the ground plane available for the radiator to work against. However, since most vehicles are longer than they are wide, the ground plane makes the antenna transmit a little better to the front and back than the sides. Mounting it on the back of a Jeep is sometimes the easiest and most out of the way place. Usually a tire rack mount will need a separate ground strap to help the antenna get enough counterpoise to work well.
The idea of a quick detach system sounds good in theory but to be honest, in this day and age, even a high end CB is basically worthless to most crooks. A mediocre stereo in your Jeep is probably a more enticing target.
I am sitting here just merrily typing along and noticed it looks like I'm writing a book! Sorry for being long winded. I can go on and on if you want but this should at least get us started. Let me know if I can help with any questions.
Hope this helps
Dave