Well, since you all have been so kind as to share your stories, here's mine.
The history: I was an XJ guy, I put over 400,000 miles on two different XJ's over the course of raising two daughters. When the last one wore out (you don't want to buy a used Jeep from me. Seriously.) I went looking for a two door, four banger XJ as a replacement. Those things are as rare or rarer than Rubicons around here. Not having much luck finding one that wasn't already trashed out, I started looking for something similar.
So, how did I end up looking at TJ's? Taking my checklist of requirements, I started to make tick marks on all the small SUV type vehicles available. After looking at all the off road capable rigs available on the used market two floated to the top. The TJ, and a Gelandeswagen diesel conversion from the shop that we were taking my wife's S class to for mechanical work. Side note, those guys do absolutely outstanding work, and their conversions are pieces of off road art. But that's a different story for a different time. So the TJ became the target vehicle. I wanted a four banger, so the SE was the only choice at that point. The manual transmission was a no brainer for me, if no other reason than the simplicity and reliability of it. Knowing that Jeep has never been particularly good at options and extras from a reliability standpoint, the SE became an even stronger candidate. Then I discovered a little detail about the ECM on the early 2.5 SE's that sealed the deal. So, a 2.5 SE with the minimal amount of options and no history of molestation was what I started looking for. Easy, right? Not so fast there Buckwheat, as it turns out, Jeep didn't sell all that many of them. A lot of them that are on the market were beat all to hell, and hadn't been properly maintained. Finding a nice, clean, unmolested TJ SE turned out to be more of a chore than it appeared on the surface. But, the game was afoot and the chase was on!
So, searching in ever widening circles and using more resources led me to a 1999 TJ SE in the Seattle area. It was on a Subaru dealership lot and had just come in on trade. Since I was going up to visit youngest Daughter at JBLM for the weekend anyway, I called them up and scheduled a look-see. The guy on the phone was pleasant, and seemed very willing to do whatever it took to get me in the door. I chalked it up big city sales tactics.
Visited Daughter, and ambled over to take a look at the SE. Blue, not green. Bummer. Grey interior, not tan. Another bummer. Air. What!? On a TJ SE with half doors and a soft top? What were they thinking. Mismatched all season tires. OK, that's fixable. Extra wide fender flares? What is even up with that? (It had wide and tall tires on it at some point) But it was straight, clean, unmolested and very low miles. When I test drove it, it drove out just fine with no obvious issues or problems. Took it back to the lot and told the guy that I liked it and would get back to him after doing a little research on it. He was really bummed out and got mildly pushy. Oh well. Fast forward a week, and I get a call from the salesman. He was asking if I was still interested in the TJ. I told him yes, it's not a bad rig and I'd like to look at it again. He told me that they would put a new top on it and a set of good matched tires if that would seal the deal. I told him that I would think about it and get back to him.
The next weekend we went up to look at it again. The salesman was super nice and extremely accommodating to my every whim. Hmmm, what's up with that? Test drove it again and all was well. They had obviously gone through it at this point and made everything sparkle and shine. Very curious. We started negotiating price and such, and he was bending over backwards to make this deal happen. At the time I chalked it up to being the end of the month, meeting quota, etc. etc. After all was said and done we were chatting, the salesman, the sales manager and I, and I straight up asked them what was up with selling this thing so cheaply and in such an accommodating fashion. They looked at each other, paused for a moment and the sales manager looked me in the eye and said "We really wanted this thing off the lot. It has been costing us sales since we took it in on trade. People would come in to buy a Subaru, see this, test drive it, and then go next door to the Jeep Dealership." I grinned, shook his hand and said "You're welcome!" Then the lot boy ran it through a car wash and ripped the new soft top before I took delivery.
And that's how I ended up with a TJ, and this TJ in particular.