"Hi, I'm a Mac!" OOPs should've stayed with Windows...

Ok I'm just going to gripe here. I've got a MacBook Pro that's almost 4 years old now, still on Tiger 10.4.11. I never had any reason to upgrade my OS; everything I've done over the last 4 years has worked fine on Tiger.
Now there's an application I want to use that requires 10.6 minimum, Lion preferred. I talked to Apple sales and tech support, and it turns out I'd have to purchase and install three operating systems to get to Lion:
1. Upgrade from Tiger to Leopard.
2. Upgrade from Leopard to Snow Leopard.
3. Upgrade from Snow Leopard to Lion.
This means I'd have to do three complete OS installs, and buy each one (Leopard sells for around $130; the other two $29 online). To make it even more fun, Leopard isn't even for sale any more on the Mac App store.
But the fun doesn't end there. The Apple techie told me I could buy the Lion thumb drive for $59 and install it from there; the catch is, I'd have to completely backup and erase my hard drive. And when I restored my original data, a lot of my apps probably won't work on Lion, so I'll have to buy and install a lot of new versions of everything.
Lion, I think I'll pass...
This is a perpetual problem with Apple products. A couple of years ago I bought a new flat panel monitor, and it turned out it wouldn't work with Final Cut Pro, so I had to upgrade that, which required an upgrade to my OS at the time...
On my Windows computer I just upgraded to Windows 7. It complained about nothing, it was only one install, and my applications I was running 10 years ago on Windows 2000 still work.
I doubt I'm the only one who's encountered this sort of problem, but unfortunately I will probably never be able to upgrade.
Scott

What exactly happens when you try?

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