if i were to get the Imac, i'd get the best base model i could buy, which would happen to be just $300 less then the quad mac pro. I don't like the Imac design.

Why? If you're getting along fine on a 9-year old machine, and you're needs aren't changing, why would you opt for the most expensive iMac? A Mac Mini will be substantially faster than what you have now - you could easily buy one and be perfectly happy.
You asked whether you
should go all out on a Mac Pro. The answer to that question is unarguably
no. It sounds like you
want to go all out and buy a Mac Pro. If that's the case, that's fine. There's nothing wrong with wanting to do so. But if you're legitimately looking for the best way to spend your money, buying a high-end iMac or Mac Pro is
not it.
You also say the iMac is slower than the Pro. This is true. But in six years, your outdated Mac Pro will be slower than the brand-new iMac you could potentially have. In nine years, your Pro will be positively outdated. If speed matters, you're further ahead in the long run buying a new machine for often.
You said you don't like the iMac design because of upgrade limitations. But that becomes irrelevent when you're upgrading the machine every three years.
Bit extreme. The OP's buying pattern is 8-9 yrs why try to change it, its obvious he's not the upgrade every 6 months/few years type. The buy/sell/upgrade method is not particularly fun either, you have to deal with the likes of craiglist/ebay where buyers can be difficult to deal with and/or try to swindle you and you often don't get a decent resale value especially in this Intel era where machine becomes obsolete the minute you press buy.
Also prices continue to go higher with new products, which means your savings will increasingly...decrease and you'd have to spend more to break even
By buying the pro it'll serve his uses for years to come and Apple won't outgrow an Intel 8 core Nehalem system anytime soon. Intel is their future and software is still catching up to hardware as it is. Granted he'd have to pay for OS/iLife upgrades.
Because a three-year upgrade cycle is universally better than a nine-year upgrade cycle. It hardly makes sense to stick to a poorly thought out cycle simply because it's past precedent.
Macs also tend to hold their resale value very well. But as I pointed out, even
without reselling the old Macs the OP's initial $3300 will last twelve years, whichis longer than eight to nine he predicts for a Mac Pro. Yes, prices will likely go up at least at the rate of inflation, but that doesn't change the final calculation much. Simply put, that money will last longer upgrading more often than it will buying one really good machine today. This is even truer if you factor in both the cost of upgrading software and the money returned by selling off the old systems.
As to timelines... nine years ago Apple was shipping dual 500MHz G5 Power Macs as their top-line machine. Nine years is a
long time in the computer world. I certainly would not want to be using a nine year old machine, no matter how good it was in its day.
The OP exresses concern that the iMac is slower than the Pro. How will he feel in eight years, when his Mac Pro is being outperformed by the future Mac Mini?
In reality, from every consideration, buying a Pro makes no sense. Unless the OP absolutely needs the power today, or absolutely needs the expandability, multiple monitor support, or options (like fibre channel card), a Pro is not a logical choice.