Well... Sometimes it's good to stretch your mind out, keeps you able to learn which is a healthy thing indeed. In general, I highly respect ClieOS' opinion, I bought my first amp (with less knowledge than you have now) based on his review and info about 4 and a half years ago, so if his review and suggestion sound good to you, I'd say you'll have a pretty good product and you'll understand what he was talking about once you get it.
Personally, I had an iBook, PowerBook G4, and a MacBook Pro, and they all had above average built-in DACs and amps. I think that was partially due to Apple's stance that their products were designed for media creation, and partially because Steve Jobs was a big music fan. I don't think your MacBook has quite the quality of my Pro model (and no optical output to connect to an external DAC that way), but my girlfriend has one like yours and it does a better job with audio than the rather noisy headphone jacks on the motherboard of the Windows machine I just built myself. So I don't think your MacBook needs a DAC as much, but it probably would benefit from one. Definitely, the 300 Ohm Sennheiser HD650 will dampen the sound a lot more than the 50 ohm HD598 you used before, and the E17's amping half will probably be only "just" enough amp for them (it's an entry-level amp, after all, that you're pairing with a venerable flagship headphone).
I dunno... I guess the good thing is, you could go ahead and buy the E17, and later if you want, you could buy the FiiO E09k desktop amp. The E17 actually docks into the E09k and operates purely in DAC mode, and the E09k does the heavy lifting as an amp. The E09k is about three times as powerful an amp as the E17, and really only slightly less "transportable" than the odd-shaped Objective2 amp you mentioned, that typically wouldn't fit in a pocket either anyway. So you can buy the E17 and see how you like it, and later on you have a nicely integrated option to upgrade to without making the E17 redundant. I think that was a pretty smart design by FiiO (though of course, any external DAC can be connected to another external amp).
You could just continue using the DAC built-in to your MacBook, or later on plug in a DAC like the HRT Music Streamer II or an ODAC (which I borrowed once, but couldn't get to work on my home built computer, I guess I am missing a driver or something). Any external DAC would do. FWIR, the E12 (Mont Blanc) has about as much power as an E09k desktop amp, which is pretty cool for a portable amp. I like my E12 very much.
If you lived in Pittsburgh, I'd be more than happy to meet and share an audition of my gear, though I haven't sampled as much as ClieOS has.