Emotional and Practical Dilemma

As one of the very few people in your age group here (I'm in my mid-20s), I can relate. I'm personally looking into buying a used Honda S2000 (or maybe a Porsche Boxster) right now.

Some of the things I've been thinking over may be of help:
1. What do you hope to achieve by purchasing a convertible? It's an important question. As you've said, it's a emotional decision and you don't want your short term emotions to confuse your long term thinking. You said it would be more "fun" - how? Faster & more agile (performance argument)? Will it attract more women (social argument)? be sure you can answer this in some specific detail.
I've (very briefly) answered the question with "I plan on (likely modifying and) racing the car at the track." There is a very detailed, achievable answer to this.

2. Practically, having a convertible is typically something that will be higher maintenance than the Prius. You'll want a covered garage for long-term (since the soft top will degrade once exposed to weather, yes even in SD). Are you seriously willing to put up with more maintenance/care? (does your lifestyle seriously support it? or are you more of a get-in-and-go car-as-appliance type?).

3. You have looked at your alternatives, right? You do realize that a motorcycle will be faster, and will likely attract more attention than any convertible you can buy. You can get a really nice bike for like $8-12k (like a Yamaha R6.....or a used Hayabusa :evil.

I'm setting aside the money argument here because I understand the desire to avoid the whole "if I had only spent a little more when I was 20, I would not have these x number of regrets" feeling. It's kind of like a quarter-life crisis. I'm not trying to insult anyone, but I just don't want you to end up like I see a lot of midlife-crisis-type guys - they buy Corvettes and Porsches (or Ferraris, I've seen those too) and just end up cruising around town alone looking kind of desperate. You spend a lot of money with a certain ideal in mind that doesn't quite work out the way you think it will.

If you're still dead-set on getting one of those two, I'd suggest (from a performance-oriented perspective) the Miata because it will be lighter and have a far larger perforamnce envelope. The Avalon, despite it's "sport" moniker, is kind of a heavy pig of a car. It will likely not accelerate or corner signifiacntly better than your Prius. Your decision to rent and evaluate is probably a really good one - so you'll get a first-hand look at the hassle/benefit tradeoff.

It's a cliche, but it needs to be repeated because so many people fall in the trap: it's a car, it does not define who you are. Good luck.

 

So all those millions spent on advertising to convince us otherwise is just wasted?

 

Hey I didn't say it can't reflect on who you are. Besides, who advertises the truth?

 

Not wasted if it works; just dishonest.

 

I thought only Old People drove convertibles nowadays.

 

Mostly the ones with 4 seats are driven by old people.