Ignoring subscriptions for the moment - assuming you're not a subscriber, and don't intend to be - you'd be losing sigs, but getting a crapload of really awesome stuff for free in return. The Gamers Seeking Gamers functionality on its own is going to be absolutely fantastic; and that's going to be available to everyone.
I think it's worth you spending some time to describe all of this in more detail, Morrus: I understand that you have some additional functionality planned, but it sounds like you're revealing bits and pieces of it and that we're not really seeing the big picture. Without that big picture, I think it's easy for us to get mired in some of the details you have mentioned, and (perhaps) to blow them out of proportion WRT possible plans that you're considering.
So, lay out the reality for what's coming (short- and long-term vision or even a multi-year growth plan, along with implementation timelines for features/capabilities, and costs of all of the above, your current costs models for the servers, bandwidth, coding, etc., etc.). Whatever you're able to share (and I don't imagine that you'll want to reveal all of the details, if only for the sheer amount of time it might take to put it all together right), that will help us to connect the dots between what features are coming, what features are here now, and what features may or may not be there in the future.
They're things we really *should* have been doing years ago - but better late than never!
Out of curiosity, are they things that the readership still wants/needs today vs. several years ago? I can find gamers through any number of free available services today like meetup.com or Facebook or whatever, and if I wanted to play online games, I could do so through DDI (or whatever WotC has) as well as
a number of other engines. Are these features ENWorld's core functionality (or, if not today, tomorrow's)?
These things may or may not be worth a sig to you; everyone will vary on that. I honestly believe that these things will add massive value to the site, and are intrinsically linked to the sitre's core functionality.
I come to ENWorld to be a member of the community, which is where I see the core functionality of the site. On the negative side of my site usage, I haven't read the front page in several years since I stopped playing 3.5 ~5-ish years ago; I don't buy/play/read the ENWorld modules/publications; I almost never click an ad unless its accidental; I miss the tag cloud functionality; and I don't read the columns unless someone links to one in GD. On the positive side, I love the old-school and other non-systems based discussions here; I continue to read Sep's Story Hour and poke around in the SH forums from time to time (and I may get around to reading Kevin's at some point...); I think the ENNies are great; I value the community specifically because many folks here aren't part of my standard old-school boards-and-blogs communities; and I've happily met several ENWorlders in RL while travelling around the country for work or at conventions (including Mark and diaglo most recently at GaryCon, and perhaps some others I'm too addled to recall offhand).
To boil this down a bit, I think that you're risking some folks' valuation of the ENWorld community as a whole with how some of your proposed changes are being perceived. That's a pretty big deal to me, and taking that risk may still be worth doing in the end from your POV, but I'd hope that you'd take the feedback and input offered to date and give some serious thought to how you're funding the site's growth toward your vision: it would suck to see ENWorld die just as you're finally in a position to make it take off in the way that you've wanted to since day 1. (And, to be clear, I think that your request for input and such have been really-well-handled herein, and that you're clearly not simply rushing into Plan X without thinking ahead, getting feedback, etc. So, thank you for that, too!

).
(And, for the record: I've been a CM and ENWorld supporter in the past, although I'm not now and probably haven't been in the past year or three, and I don't think it was for more than a year or two).