Thinking of going in a drastically different direction (Jeep vs. S2K)
Had a 2010 JK Unlimited. It was great to know that I could take the top off. Sure it wasn't fast and the gas mileage sucks, but I did enjoy being able to drive around with the top off and it was great being able to see over cars. 
I do miss it. But didn't really use it as much as I thought I would.

I do miss it. But didn't really use it as much as I thought I would.
I thought about that, and I will still think about it. I just went on Jeep's website, and it looks like a well-optioned 4-door Wrangler runs about the same price as my TSX. I'm not sure about how tolerable the Wrangler would be on a 4hr road trip though. The loss in gas mileage would be offset by the fact that I don't need premium fuel, so that's a wash. I've gotten really used to the creature comforts of the TSX though, so I wonder if that'd be hard to give up.
you could always keep it as a get-a-way car.
When you need time to yourself, you can always jump in the car and take some time for yourself. Would say drop the top, but you have a hardtop.
The decision, I'm sure, is going to be hard. The cars are so different, but since you have a family and enjoying dropping the top. It'll probably be easier to make a decision.
If you do decide to trade in the TSX for a Jeep, I'd go with a brand new one. Better tech, better engine, better fuel economy. This would help with your creature comforts.
Also, don't forget that the value of jeeps stay pretty high. I bought mine for 31 and sold it for 26.5. Had it for about a year and a half. I could have held out for a bit and sold it for more but was trying to get rid of it, so I could actively look for the car I have now.
Couple of things that was irritating for me. I had to get the driver side window seal replaced 4 times under warranty. The plastic windows can get creases in them pretty easy, but can be alleviated by taking your time with them. Gas mileage, but it's to be expected. No locking gas cap. Oh yeah! There are too many parts you can buy for it.
And definitely much cheaper than the S.
But all-in-all, go drive one.
If it speaks to you, then go for it.
When you need time to yourself, you can always jump in the car and take some time for yourself. Would say drop the top, but you have a hardtop. The decision, I'm sure, is going to be hard. The cars are so different, but since you have a family and enjoying dropping the top. It'll probably be easier to make a decision.
If you do decide to trade in the TSX for a Jeep, I'd go with a brand new one. Better tech, better engine, better fuel economy. This would help with your creature comforts.
Also, don't forget that the value of jeeps stay pretty high. I bought mine for 31 and sold it for 26.5. Had it for about a year and a half. I could have held out for a bit and sold it for more but was trying to get rid of it, so I could actively look for the car I have now.

Couple of things that was irritating for me. I had to get the driver side window seal replaced 4 times under warranty. The plastic windows can get creases in them pretty easy, but can be alleviated by taking your time with them. Gas mileage, but it's to be expected. No locking gas cap. Oh yeah! There are too many parts you can buy for it.
And definitely much cheaper than the S. But all-in-all, go drive one.
If it speaks to you, then go for it.
I made the same switch - I've had 2 S2000's, and traded from an 07' GPW/Red, to a black Wrangler Sahara 2-door. I have my Jeep modified as much, if not more than I'd had my S2000. With 33" Trail Grapplers, 18" Rock-Stars, a 3.5" lift, custom black emblems, and 5% tint - this thing get's compliments everywhere I go - much more than the S2000 ever did with LM's, NSX-R red "H" emblems, and a full OEM body kit. I say go for it. I miss carving the road in my S on occasion - but I love the freedom the Jeep allows me, and the versatility of the functional rear seat. Good luck with your choice!
Do what I do; daily the jeep and weekend the s2k. If you get rid of the s2000, you will be wanting another one later. Believe me, it happened to me, and many other that I have seen. The only difference between now and when it happened to me is that they are now out of production and getting harder to find decent examples. You know your car and the kind of shape its in. Consider if you want to take the time to try to find another used one that you dont know the history of.
Do what I do; daily the jeep and weekend the s2k. If you get rid of the s2000, you will be wanting another one later. Believe me, it happened to me, and many other that I have seen. The only difference between now and when it happened to me is that they are now out of production and getting harder to find decent examples. You know your car and the kind of shape its in. Consider if you want to take the time to try to find another used one that you dont know the history of.
you could always keep it as a get-a-way car.
When you need time to yourself, you can always jump in the car and take some time for yourself. Would say drop the top, but you have a hardtop.
The decision, I'm sure, is going to be hard. The cars are so different, but since you have a family and enjoying dropping the top. It'll probably be easier to make a decision.
If you do decide to trade in the TSX for a Jeep, I'd go with a brand new one. Better tech, better engine, better fuel economy. This would help with your creature comforts.
Also, don't forget that the value of jeeps stay pretty high. I bought mine for 31 and sold it for 26.5. Had it for about a year and a half. I could have held out for a bit and sold it for more but was trying to get rid of it, so I could actively look for the car I have now.
Couple of things that was irritating for me. I had to get the driver side window seal replaced 4 times under warranty. The plastic windows can get creases in them pretty easy, but can be alleviated by taking your time with them. Gas mileage, but it's to be expected. No locking gas cap. Oh yeah! There are too many parts you can buy for it.
And definitely much cheaper than the S.
But all-in-all, go drive one.
If it speaks to you, then go for it. 
When you need time to yourself, you can always jump in the car and take some time for yourself. Would say drop the top, but you have a hardtop. The decision, I'm sure, is going to be hard. The cars are so different, but since you have a family and enjoying dropping the top. It'll probably be easier to make a decision.
If you do decide to trade in the TSX for a Jeep, I'd go with a brand new one. Better tech, better engine, better fuel economy. This would help with your creature comforts.
Also, don't forget that the value of jeeps stay pretty high. I bought mine for 31 and sold it for 26.5. Had it for about a year and a half. I could have held out for a bit and sold it for more but was trying to get rid of it, so I could actively look for the car I have now.

Couple of things that was irritating for me. I had to get the driver side window seal replaced 4 times under warranty. The plastic windows can get creases in them pretty easy, but can be alleviated by taking your time with them. Gas mileage, but it's to be expected. No locking gas cap. Oh yeah! There are too many parts you can buy for it.
And definitely much cheaper than the S. But all-in-all, go drive one.
If it speaks to you, then go for it.
I don't know, the more I think about it, the more I think I'd rather get rid of my TSX like someone suggested, and keep the S2K as my "fun" car. They do hold their value remarkably well. If I replaced my TSX with one, I'd be looking for a new Jeep like you mentioned rather than a more raw used one. I think I'll need to test drive a loaded Ultimate and see what I think about it.






