I have had several people now tell me they were so frustrated with the Vista upgrade process they were seriously thinking of buying a Mac and I've suggested that they wait. Because the Vista experience will get better and because Apple's Leopard will have a stronger bite than Tiger, the current MacOS version and it is due soon. It is not yet clear what the Leopard upgrade experience will be, but I'll bet it will still be better to get it preloaded if you have a choice. More importantly, I'm still expecting a hardware refresh to go with the new OS.
A spring surprise
Apple is apparently planning to unleash Leopard in March. This would be two months into the launch cycle for Vista, too early for a major service patch and probably at the height of user frustration surrounding support and compatibility issues. If I were to guess, I too would conclude that the Vista market share will be most vulnerable just about at that time. After March, the product should start to come back around; by the end of August, it should be comparatively solid, so the time to hit it, and hit it hard, would be between March and July which supports the rumor of a Leopard March release.
This could backfire though, if Leopard isn't mature enough. Pulling in a bunch of Windows users who will be frustrated with the differences in the Apple UI anyway and hitting them with Apple bugs could quickly turn a victory into defeat and new converts aren't as likely to swallow the initial problems as the traditional Apple fan audience is. Still, Leopard isn't a major release like Vista and the opportunity for breakage is much less as a result. So the odds are in favor of it providing a comparatively better initial impression.
Built to kill
Apple has been positioning Tiger as a better Vista for some time. The YouTube video with Microsoft at CES describing Vista and a screenshot of Tiger actually demonstrating what he is describing is a classic example of that. Apple is expected to continue to build on this message through March - that Tiger is a better Vista. In fact, when Leopard launches, it will seem that it will be a product that is a generation ahead of Vista. That isn't a bad strategy at all and, depending on what Leopard actually has in it, could be very powerful, particularly with early adapters.
One part of Leopard that will clearly be showcased is embedded core animation, which will make backgrounds, screensavers, and third party application stunning to look at. While many refer to this as "eye candy," it should make the product look more advanced than Vista given that the only feature that can possible close this gap, Windows DreamScene, is only available with the Ultimate Edition and it is still not in final form. I've been using it for some time and I've got to admit, it really makes my background pop.
Evidently, both iLife and iWork 2007 were not announced at MacWorld so that they could make better use of this core animation engine and I understand the result could be stunning. Recall that the connection of Office 95 to Windows 95 made both more popular and that this was not done with Office 2007 and Vista either from product or brand perspective. It looks like Apple has learned at Microsoft's knee something that Microsoft itself may have forgotten with their latest releases. Office doesn't embrace the new Vista UI very aggressively, apparently attempting to bridge XP and Vista, and the name still uses the date convention. Even though they were launched together, the combination isn't as powerful as it could, and probably should, be.
For business users, Leopard is supposed to have a much better native Exchange integration. Coupled with an already rather nice Active Directory support, it could work much better in a Microsoft shop than and previous version of the OS. Where I've seen the Mac fail in business deployment testing is with Exchange integration and, if they have truly fixed this, this could be a game changer.
Finally, it is clear they have done something to improve dramatically Windows application support and have specifically been doing something with regard to gaming. Common sense tells me that there may be a better integrated virtualization but the buzz suggests something better. I don't have a good read on this but I think it will be more and it will be different from what we have been expecting. They know about the OS/2 mistake and are unlikely to repeat it by trying to embed Windows inside Leopard.
Will it work?
Even though there is little doubt that Microsoft will see this coming and could prepare a response, the company is relatively stuck on the track it is on. Modifications and improvements into Vista, outside of bug fixes, aren't likely to surface until well after March.
Microsoft undoubtedly believes that their historic protection of massive backwards compatibility with applications will protect much of their market share and that is probably an accurate belief, but all Apple has to do is grow their own share dramatically to win. And, if analysts look at Microsoft's future and see a long trend of market share erosion, Microsoft is likely going to see its own valuation suffer. On the other hand, most of the major Windows vendors are planning mid-year product refreshes and, based on what I've seen, these will give Apple a run for the money. The Toshiba R400 and HP Touchsmart PCs are early examples of this and arguably showcase that the OEMs, at least, can push back on Apple and push back hard.
The long term problem for Apple, however, is that they can't deliver a killing blow and are probably really going to upset Microsoft's management, possibly enough to make some long overdue changes to how Microsoft approaches this market. Let's call it a really nasty slap.
Microsoft has done some rather impressive repairs to its own OS organization and is expected to have a major refresh out in 2009. That refresh could have, as a goal, a counterstrike and Microsoft is capable of delivering a killing blow if they were to focus their efforts and this Apple slap will, at the very least, get their attention.
So I absolutely think Apple will catch the giant sleeping, the danger is that this could focus Microsoft like a laser on them and a focused Microsoft, as Netscape discovered, is still potentially a very scary thing. Then again, we kind of said the same thing when Microsoft slapped IBM.