Windows Vs Mac For Web Design
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The main benefit to getting used to working on a Mac is that most design/ad/marketing agencies are Mac based still, most places even the account people are walking around with airs or macbook pros and ipads vs windows/android machines. Mostly just because they always have been and that's what everyone is used to. There's not really any legitimate reason not to use windows at this point for any kind of design (good luck convincing art directors that though), but there's really not any legitimate reason to switch either. Except that the learning curve for the art directors and designers who have been on macs since college generally isn't worth it. I also don't really agree with your economics comment.
Entry level macs are not overpriced at all for what you get. Maxed out configurations are overpriced as shit (especially the towers. It's almost criminal that they're still selling them for those prices). Yes you can go on newegg and grab something with similar numbers on the box for less, but that doesn't make it the same. I know it sounds douchey but there's more to macs than the specs.
I'm a PC user(Windows) and in my experience of working with agencies that relied on Macs, there were no benefits or drawbacks. Actually the only 'problem' was when i needed a font and they would constantly send me files in the wrong formats. For me there is more to PC then just specs. I'm the kind of guy that likes to make and build things for himself. I build quite a powerful machine earlier this year and i just love the experience - selecting the parts and then putting them together. I don't get it with a mac. That's just me though.
I understand all the reasons why someone wants to own a mac, but they aren't good enough for me. I prefer to answer this as a hardware question. My ideal setup, what I'm posting from now, is a juiced up MacBook Pro that also has Parallels/Windows installed. I'm a stickler for having all the tools at my disposal, and designing for all the audiences. That being said, I do think it's quite obvious that Mac hardware is substantially better than the shitty flimsy discount PC's made with low-performance chips and crappy plastic bodies. And yes, I am willing to pay a higher premium for this. Some of you may not be.
I also don't care to monkey with the guts of my computer. I'd rather just give someone a lot of money to get a thing that works well. I use an iMac at work and Windows 8 at home. In terms of the OS, I'm very big on keyboard shortcuts so the differences are pretty minimal. Windows PCs are typically more prone to 'act up' due to all the garbage that comes bundled with downloaded software and the computer itself. I think a clean, properly maintained install of Windows is just as reliable as OSX but that's not the Windows that most people end up with. Apple computers usually work well without bothering you.
The hardware on the other hand, namely the displays, are where the true differences lie IMO. Apple typically uses high-res IPS panels that are accurate and don't change colors at different angles, while PC manufacturers like to skimp.
The display is pretty crucial when it comes to any kind of digital design. So combining the element of minimal crapware, consistent performance and the displays, people have good reason to lean toward Apple. It's a gorgeous peice of hardware they'll rarely be concerned about. I personally keep my Windows machines clean and running well, so I wouldn't ever throw down on a Mac (the one at work is company-owned). IMO, 1500-2500 is an incredible amount of money when it comes to computers and with that kind of budget I would buy a 400-500 dollar machine and put the rest into two or three decent monitors.
As a developer, for my workflow, I find multiple monitors to be invaluable and that's where I feel my money would be best spent since hardware and OS is typically not an issue for me. I do webdesign/development work from home. I have a few machines. Getting notepad ++ for mac. Windows 2007 running on a microserver - for offline development, NAS Windows 8/XP laptop for testing/very cheap vs mbp on the move But as of the beginning of 2012 Hackintosh as my main machine. Cheaper(!)/higher spec that tower mac plus 3 monitor outputs However.