It’s been a while since I’ve done a “Let Me Tell Ye” post, so just a reminder / warning that in addition to some useful computer tips, you’re going to get some snark.

I’ve been using Windows XP since late 2001, shortly before I switched to Mac (basically WindowsME was what made me switch, and by the time XP came out, my mind was made up, but I bought it just to get me through the last couple months before I could afford a Mac). Since then I’ve always had an install of Windows on my Mac, which until this week has always been XP. I also have a gaming rig, which also runs XP. I recently hit a point where I felt that Windows 7 had been around long enough that I trust it will be compatible with my games and peripherals, and will provide better performance with modern hardware (such as my 4GB of RAM). Over the summer it made it to the top of my short list of things to buy when I get a little money.

As part of preproduction for my upcoming tour, I’ve been focusing on Windows a little more than usual because I have a PC-using assistant. So I thought it might be a good idea to take the opportunity to buy Windows 7 now, so that if we ever need to do something Windows-based, there won’t be a chance of it not working because I’m using an obsolete OS.

So let me tell ye, without further ado, my experience installing Windows 7 on my MacBook Pro, over an install of XP. I wrote this throughout the process:

Background

So here’s what I’m working with:

• mid-2010 15″ 2.66GHz i7 MacBook Pro
• 4GB RAM
• Mac partition with Snow Leopard 10.6.4
• Windows partition with XP SP3 32-bit
• Windows 7 upgrade disk (which comes with 32-bit and 64-bit install disks, I will be attempting 64-bit)

The Begininng

I made sure I had the latest Boot Camp update (3.1) for Windows 32 bit, which gets run on XP before the update. Honestly I’ve never been quite clear how Boot Camp works, but I know it’s necessary for driver support, so I need to make sure that’s done first, and everything I’ve read says this is necessary before installing Windows 7 in Boot Camp.

Step 1: Open the Box

When I had recovered from the optical spectacular that is the hologrammed install disc, I found a loose piece of paper in the box making it sound like if I’m going from XP to Win 7 my life is going to be miserable. So I grabbed one of my spare hard drives, reformatted as NTFS, and got ready for an ordeal.

The instructions sent me to a website to download a helper. I carefully typed in the address (in IE, cause I figured they’d do something stupid like make that important). But because I was using IE, it didn’t send me to the page because I didn’t put “http://”. Sorry. I must have been looking for that other internet, so it’s a good thing you sent me to Windows Live Search instead, where the only result happened to be the page I was looking for.

The first instruction cautions me that when I start the installation I need to select the “custom” option if installing from XP. Well, I know the OS is old. To me it feels like just yesterday because I switched to Mac just a few months after it came out. But let’s not pretend that the only OS in between didn’t suck. Plenty of smart people, and lucky ones who didn’t need to buy new computers, skipped over Vista. So stop acting like those of us still on XP are some kind of technology-shunning aberrations. Thanks.

So it checked that my computer is compatible with both 32-bit and 64-bit versions of Windows 7. Then I was instructed to download the optimistically-named Windows Easy Transfer. Now this “easy” transfer doesn’t actually transfer all your stuff intact, it takes your files, but you need to reinstall your programs. That seems like a pretty smart idea when changing OSes anyway, but I’d call it more like, “We’ll Kinda Help You Transfer.” Like if a friend offers to help you move and all they do is hold the door open for you while you carry the stuff out, and then leave you at the door to your new place with a list to help you remember all the stuff you have to unpack.

While Windows analyzed my computer for ease of transfer, I heard my Mac reboot. Apparently spontaneously and unintentionally, because when I restarted it said the bit about “Windows has recovered from a serious error,” and actually used the word “blue screen” somewhere in there. I wish I had been looking, it would have been a great photo op.

With this comforting sign before I’ve even begun my major upgrade, I started over with the “Easy Transfer” program. That time, it alleged it was able to back up all my files. Then while doing absolutely nothing, my computer initiated a shutdown. It wasn’t a blue screen or anything, just a very calm “windows is shutting down now,” like any other shutdown, except that I hadn’t asked for it. Now I’m hoping that this install will wipe everything, cause obviously it’s F’ed up.

Side note: Dropbox is being real slow. I wonder if Evernote might actually be faster for transferring single large files. I’ve been researching and downloading the files I need from my other computers and then just putting them in my DropBox so I can get them from the machine I’m updating.

So finally I put in my install disc. Because I’m going from a 32-bit OS to a 64-bit one, I have to boot directly from the CD, it can’t be done with the OS loaded. Check out this futuristic loading screen. I’m so excited to be computing in the 21st century!

Of course the progress bar has no bearing on actual progress and freezes at 100% for an uncomfortable period of time. Maybe I should just play a game of Civ 4 or something while I wait so I’m not tempted to mess with it. I’m not kidding, that’s what I’m doing. Let’s see how many millennia I can get through while it loads files.

…I started in 10,000BC, by the year 435AD I gave up.

I came to discover through more googling that apparently while you can upgrade from XP to 7, on a Mac it’s not so easy. Something about how it boots off the CD, and the differences in how Macs and PCs boot. The only path seemed to be to do a clean install. Which is more or less what it was going to end up being anyway, as I understood it, so I didn’t find that to be a problem. Back to the same “loading files” screen… This time I got beyond it. There were even some greater-than-1-bit graphics.

Finally the whole thing installs beautifully. Then I go to put in my product key and it says it’s invalid. I come to find out that you can’t do a clean install from the upgrade disk, despite the fact I had read that you could. It doesn’t bother to ask you for a valid XP product key or install disk. So now I’m back to square one of reformatting and installing XP (which also means an upgrade to SP3 and all other updates since then) before I’m ready to try the upgrade to 7 again.

Total elapsed time so far: 3 hours.

5 hours in, I am now back where I started. I got interrupted when The ’70s called, asking for its progress bar back. I said it was still frozen on my screen and I’d return it when I got it unstuck. I even tried using the 32-bit install disc, thinking that would be an OK solution temporarily until I can figure out how to fix this. But that still told me it needed to boot from the disc, and still froze in the same place.

I googled some more, and found that getting stuck on “Windows is loading files” is very common, for Mac users and regular PC users alike. One lucky fellow I read about said he found the solution to his problem in that after randomly restarting about 10 times, all of them resulting in the process freezing at “loading files,” he was rebooting again, giving up and trying to boot in OS X and suddenly it worked. Mine had only failed about 3 times, so I decided this ridiculous “solution” was worth trying. And on the fourth time, suddenly it loaded fine. So far so good. Back in the 21st century.

If I EVER have to go through this process again I will not be happy. I would just like to point out that this is one of those situations where legitimate users get punished. I can only imagine how many people have installed pirated copies and had none of these troubles because they could have done the clean install and avoided the incompatibilities with XP.

6 hours and counting — it accepted my product key and I’m using the OS. Haven’t installed Boot Camp drivers yet, but it’s run its first software updates.

Boot Camp installed, so I can now see it in full resolution. This is the ugliest OS I’ve ever seen. I don’t think it’s supposed to be. When I start tinkering with settings I’m sure I’ll figure it out. Right, Microsoft?

Well I found the personalization settings. Yeah it does get a little more attractive with all the Aero effects turned on.

The default wallpaper is hideous. I’ve always thought Microsoft was pretty good about that in the past. I don’t like any of the built-in wallpapers. I decided to start with an orange theme, and found a wallpaper I liked online. I’m not sure I like it, but I would have died of boredom with the default theme on. My buttons still turn blue when I mouse over them, and I don’t see a way to change that.

Overall performance seems good. I like that I finally have an OS for gaming that can see all my RAM. I haven’t done a lot of gaming yet, but what I have done feels very good. Sorry, I don’t have any before-and-after FPS comparisons.

So to summarize, if you run into this problem that a lot of people face with the install freezing at “loading files,” the highly sophisticated solution is to just keep doing it over and over and one time it might work. Which, incidentally, is also the definition of insanity.

Parallels

After getting everything up and running in Boot Camp, I checked it in Parallels. I had to go through a bit of a reinstall, but Parallels handled that pretty well. There was a point where Windows tried to do a repair on itself and failed, but I used the tried-and-true method of “just try it again” and it worked. I wasn’t given any grief about activation. With virtualization you can have problems because the OS sees your machine as having different hardware in Boot Camp and Parallels, and thinks you’re a filthy pirate trying to install it on two different computers. I actually don’t know how they check it, but I’ve never had it reject me since 2007, when I had to call a number and explain to them what I was doing. The nice woman I spoke to in India cleared it without giving me any argument, so it wasn’t a terrible experience. I’m just amazed that as many times as I’ve messed around with that install, it’s never happened again.

Performance in Parallels is something I’ve been struggling with for quite a while. I had finally gotten it to a level I was happy with, which involved devoting less than half my RAM to the virtual machine. Unfortunately Windows 7 requires 2GB of RAM, so I have not tried giving it less than that. I’m still experimenting. I really would like 8GB of RAM, but it’s still pretty expensive.

I wish the install hadn’t sent me on a wild goose chase, but when it was all done, I was able to get the OS I wanted installed, and so far I like it. Of course I won’t really be spending much time in it, but I like what I see so far.