Well, Metastock (end-of-day, dunno about real-time, but I assume the same) won't run in a VM without some tweaking. I went through the install only to find that it complains that it doesn't run in a VM when you actually run it.
Seems to be a limitation of the third-party licensing enforcement solution that they use. Lame.
There is a way to run it in a VM, but it involves a global setting for the VM that may adversely affect other programs. (I think performance.) I haven't gotten around to trying it. Very disappointed that Metastock doesn't disclose this prominently. I was hoping to shut-down my Windows box.
I would definitely quiz each vendor extensively on this.
Dunno who you are going to trade with, but you might find that the software provided by Interactive Brokers is adequate. And you wouldn't have to spend $100+/month on data fees. It's had several years of development now, and they are still constantly adding new features. Though it started as just an order-entry platform, it's gotten more and more sophisticated for charting. And it's Java, so will run natively on OSX. If you haven't chosen a broker, IB is a first-class operation, and pretty unique in the ability to slosh funds transparently between stock and futures trading accounts, access to a wide variety of international markets, super-low commissions, etc.
If you do go with VMWare, install the 64-bit version of Windows 7 and give it 1.5GB of RAM out of a minimum of 4GB total. 32-bit Windows 7 will take somewhat less memory, but will run slower, due to inability to run full virtualization. I've found 1.5GB to be the sweet spot, at least for me. I don't see a signification performance increase beyond that, but it depends on what application you are running, of course. I wouldn't expect stock trading platforms to need a lot of memory.
BTW, I'm a programmer, and have written automated trading software (initially, using RealTick III, and later using direct dedicated feeds from the exchanges/ECNs, ITCH/OUCH, co-located server at ISLD (when there used to be an ISLD) etc. We were probably one of the first to do what is now called high-frequency trading (didn't have a name at the time) but I've been out of that for a few years. Partner was too stingy with hardware spending and didn't believe the magnitude of the "war of escalation" that I predicted... But we pulled in several million on an initial $50,000 capital outlay before it was over... I'd guess a $1M investment just to get into the game now, so if you're thinking high-frequency - don't.