Would I be stupid to trade in?

I currently drive a 2007 Honda Civic SI with about 159k miles on the clock. I love the car, though it has given me quite a few issues in the year I’ve owned it (starter went bad, alternator and battery, warped brake rotor, suspension is very clunky and would probably need replaced if I kept the car), it has always been a blast to drive and a great daily driver.

I currently have the opportunity to trade in for a 1998 Porsche Boxster. I have always been a fan of the boxster but never really looked into getting into one. A local dealership has one that is very clean, though it has 130k miles on the clock, and is the tiptronic automatic instead of the 5-speed manual. The car was very well maintained and even had the infamous IMS bearing and rear main seals replaced. The interior could use a little TLC but otherwise the car is a prime example.

Part of me is ready to pulled trigger and take the Porsche home. The dealership offered me a more than fair trade in for my SI, more than I was expecting to get. There are, however, a few hangups that are making me hesitate:

1.) the cost of upgrading. Even with a generous trade in offer, I would owe an additional $6900 on the car out the door. This is somewhat tough to swallow because the SI is fully paid off.

2.) the transmission. I love driving manuals, but I’m not the type of person who NEEDS a manual. I would be happy driving the tiptronic, however I can’t help but wonder if I would regret it later down the line. It’s a great transmission for cruising but it is definitely sluggish compared to a manual or even a newer dual-clutch style auto ( I owned a 2016 S5 with the auto and loved it).

3.) remorse. Though the Porsche is undeniably the cooler and more enjoyable car, I absolutely love my civic SI and worry that I might miss it. If it were feasible to have both I definitely would, but at this time in my life I can only have one daily driver. I am not concerned about the Porsche being less practical, more just that I may regret my decision and getting rid of the SI.

Obviously this is a decision I have to make for myself, but I would love to get some input from others. Should I just pull the trigger and enjoy myself? Would it be worth trying to wait it out and find a good manual example? It seems like prices are just going to continue going up for these cars. Yes the car would be a daily driver and I live in the PNW. In the winter I would slap on a set of snows and send it. Also, the maintenance doesn’t necessarily scare me. Of course I understand it will be more expensive to drive and maintain than the Honda. I’m pretty comfortable working on cars so I would be doing all the basic maintenance (oil, filters, plugs, fluids). Any advice or thoughts are appreciated. TIA!