Why not just upgrade the W500? It'll be far cheaper than going to Mac and renting out a server. For disk space you could get the SATA HDD bay for storage and memory is simple to upgrade on Thinkpads (and better it doesn't void your warranty, because Lenovo doesn't assume your an idiot).
Didn't know that. I thought as their mobile workstation it'd have a higher cap than that. It is a little old I guess.
Personally I'd go with a new Thinkpad. MBPros are nice but the new ones are completely non-upgradable which is a real deal breaker. I've used a T500 for a little over 4 years now with nothing but more RAM, a new SSD, and a storage bay HDD.
The SATA interface won't make a significant difference. It does at the margin but not for normal use. If you are going to use remote servers why upgrade at all?