As of recent since the First upgrade window has shortened. First class upgrades have been much harder for me to come by and I have since been booking MCS for $400-$800.(JFK-LAX)

Granted you get priority boarding, free food/drinks and bag but it occurred to me recently when looking at tickets, I could technically buy 3 MC for less than or equal to the cost of 1 MCS seat. There has been quite a few times I have booked MCS and someone has foolishly either last minute booked or paid to upgrade into an MCS middle seat, in turn making the trip not comfortable at all for me.

I am debating to now, instead, book two MC seats for myself (which with all the food I can eat, drinks I can drink, movies I can watch and the checked bag fee is still substantially cheaper than 1 MCS.) I figure the minimal legroom/pitch I give up can be made up for by putting my legs into the empty middle seat and having some breathing room to the side of me. Anyone have any thoughts/ideas on this?

Yes, I think that might work. But you can't just book the seat and expect it to go untaken. If the party for whom the seat is reserved doesn't show up at T-10 minutes, they will give it to standbys, or anyone who wants to upgrade to it.

I know the other airlines have a method to book the extra seat, and there's some talk on this message board about how to do it. You need to book it with something like "EXTRA SEAT" as the name or something like that. Search around. You might want to call VX customer service to see if there's a procedure for it.

You can buy two seats for yourself if you're a POS, so I'd guess you can do so even if you're not:

http://virginamerica.custhelp.com/cg...i=&p_topview=1