Digital Doubts

I've come to realize that I really, really need to move into the 21st century--at least when it comes to art. I still want to work in traditional media, but adding the basic tools of a Wacom tablet and Photoshop would save huge amounts of time and frustration. For one thing, I could take rough thumbnails from my sketchbook and develop them on the computer instead of trying to enlarge or alter the sketch by hand. (I always lose the energy of the original idea.)

However, there are a few problems I'm still mulling over:

Old Laptop + Upgrades vs. New Laptop

My laptop is seven years old. Last summer the hard drive crashed and a friend replaced it. But the operating system is old, and I have a suspicion that it's only a matter of time before the laptop dies for good. Should I try to upgrade to Windows 8? Or just buy a new laptop?

Photoshop CC vs. Corel Painter.

Everyone I've asked seems to prefer Photoshop to Painter. Painter has a reputation of being difficult to learn. Painter costs around $400. Photoshop is now only available by monthly subscription from Adobe-- the last non-subscription version, Photoshop CS6, costs around $700. Arg.

My Beautiful Tablet

No debating here.  I'm pretty much sold on this tablet.  It includes Photoshop Elements and a free trial of Painter.  (I still need an operating system that can manage either of those.)

If anyone has any advice to offer in regards to software and laptops, I'd appreciate it.