OK, I'm wading into shark-infested waters here, so I'll try to be as fair as possible. I've recused myself from any TGM threads on the Theme Parks board, but I'll share some thoughts with the
DVC crowd.
I've subscribed to TGM twice, including prior to our trip last December. I wouldn't call myself a compulsive planner, more of a compulsive reader. I tend to absorb as much info as possible and then make my own educated decisions on the fly.
Anyway, here are the things that I didn't care for regarding TGM:
1. It feels very disorganized. When you read a book, the book has a flow to it. When you read TGM, he does have individual pages that address different topics. But, every page seems to have a dozen or more links to OTHER pages with related info. Just trying to read up on a single topic seems to send you running around in circles trying to hit all of the cross-linked pages.
Also, most of his pages have revision dates, but often they don't include a year. So if you see an article posted "April 4", you can't tell if it was revised yesterday or if the information is a year old.
For an example of both of the above, check out this link:
http://www.tourguidemike.com/articles/categoryDetails.asp?categoryId=15
Lotta clicking to get from one article to the next, and no clear indication of when any of them were written.
2. For whatever reason, Mike had ZERO info posted about Saratoga Springs as of January of this year. For every other resort he has info on dining, recreation, resort photos and so on. But the Saratoga Springs pages sat there for months with a simple message that read "this is just a test..."
Mike and I politely exchanged messages about this. He was correct in saying that the site still has a LOT to offer, but it just rubbed me the wrong way to see that it was apparently such a low priority for months and months.
3. I think his "Automated Vacation Planner" is a bit mis-named. Perhaps I didn't read well enough when I first subscribed (which was shortly after the site went live a couple of years ago), and hopefully it is better described now. But what I thought I was getting was something that would allow me to enter our ride and dining preferences, and would then spit out a custom itinerary for our trip. Not too much to ask with today's technology, eh?
In reality, it doesn't do anything to create custom touring plans. It will give you a nice printed list of the attractions you select, and recommend times to visit. You'll also get links to generic pages with more touring info.
Admittedly, this is probably a case where my expectations where just too high.
With that said, I think there are some people who would very much benefit from TGM:
1. Those who visit during peak seasons. Reportedly his touring guidelines can't be beat. We always travel during the off-season, and I found the info to be little different that anything I've seen elsewhere.
2. Those who tour commando-style (see above.)
3. Those who want the most up-to-date info available. In addition to the web pages, Mike also patrols his own set of message boards answering guest questions time-permitting.
I don't want to give the impression that I never learned anything new from TGM, because I certainly did. I'm just not sure that the cost / benefit trade-off was very advantageous. I couldn't honestly say that the tips I did learn were worth the cash + time investment.
But, many people don't spend 20+ hours week week reading and posting on the DISBoards, and many aren't approaching their 5th trip in 3 years. So feel free to filter the above accordingly.
I'm another one that has renewed membership 3 times. I've been to WDW more times than I know right now....but my past few visits using TGM have been far and away THE best 
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