Planning on using one or the other for games, but not sure which is better? Any help would be appreciated. Also, how easy is it to get windows updates using either? Just a matter of updating windows like normal?
Windows updates work fine in either case. No problems whatsoever in my experience using both options.
Personally, I prefer to game on my iMac with these options in this order:
Native ports (Feral, Aspyr, etc.), Blizzard, EA, etc.
Wineskin/Boxer ports I do myself. I was resistant to try this at first thinking it would be too much trouble but really it isn't, for me at least. I enjoy doing them and get a certain feeling of getting away with something, running them on my iMac without reboots, etc. I've had very good experience with both options, but it has been with older games so far. It only took me a couple days of reading the instructions, using Wineskin and Boxer depending on the game and looking up on AppDB, etc. tips and whatnot for anything that didn't work out of the box. In most cases I did have to do some tweaking but I learned a lot about porting games using these tools in the process and enjoyed it actually. The results were excellent too. I am playing Halo Combat Evolved currently thanks to Wineskin without having to start a virtual machine or reboot.
Windows XP with Parallels 8 for older games that run better on XP or don't run well on multicore systems. I set the VM up for single core. This works great for older titles that do not run flawlessly with Wine.
Windows 7 with Parallels 8 for newer Windows games that require dual core CPU and are more demanding. However, I do think this option is limited by performance issues running in a virtual machine, the newer the game is, etc. For example, anything requiring DX 10 isn't going to run fast enough in probably most all cases even though Parallels 8 now supports DX 10. DX 11 is not yet supported at all. They have a lot of work to do with DX 10 performance-wise. This option is for when a newer title doesn't run flawlessly or close with Wine but will run well in a VM.
Last up, when all else fails I will for now reboot into Windows 7 but I greatly dislike leaving OS X and bothering with this. I am currently working through a backlog of games that only work well this way and once I am done I will be deleting the bootcamp partition.
I do not buy Windows games anymore. It's Mac or bust from here on in for me personally. I find that enough good new games are coming out for Mac now that I don't need Windows anymore but this is in part because I plan on buying a PS4 for anything coming up in the way of AAA games that isn't available as a native OS X release.
Since I own the Windows licenses, I'll be happy in the future to have the option to use Parallels for the large library of games I own that run well in virtual machines. I might consider a Windows game in the future if there is no Mac version available only if I find out that it will run well with Wine using Wineskin. Otherwise, it simply isn't worth it to me. I did not buy a Macintosh so I could have an Apple computer running Windows 7. I hate rebooting.
Did I mention I hate rebooting? ;-)
Oh yeah, honest I am not a hateful guy generally at all but... I hate Microsoft too. I won't ever be purchasing another Windows license. I'm done with them.