I have personally owned almost every jeep model. I have owned CJ3A 1976CJ5 Levi's edition XJ x3 YJ x2 TJ x2 and now a 2012JK. I have not owner a CJ8 and like the idea of a convertible jeep pickup. If Capt. Is looking for a cj type jeep im going to say go with a CJ8 its not seen every day and also versatile.
You would be surprised the cars I have walked away from through the years in my buying history, just because of little things like. seat comfort and fit and finish and mechanical reliability just to name a few. If the car does not fit you must acquit, ok that's not a good saying but you get the idea.
You can research things all daylong but apply a little personal experience into the formula, and you will have a little more fun.
I like your idea better for a Miata. I was going with the 50s Diner Seen.
Now 55k for the Whole lot in your photo. Now that is 55k worth of cars 5-8k for a nice Toyota truck and 30k+ for one of the better DeLorean on the market. Now that's 55k well spent. And leaves you a little left to by a life time supply of Pepsi and or TAB soda. Got to love the Back to the Future trilogy!