I'm a guy that's perfectly in your target audience, and knows at least 5 others in similar situations. We've spent lots of money on dancers, sites, etc. Most of us don't really want to cheat on our wives. Over the past two years, my external game has gotten a lot better. I've picked up a few girls' numbers just in the last month, but I'm never going to call. But promising you can raise my conversion rate at home? F*ing genius.
Let's be clear: You're selling sex. Do you have any idea what married men spend on sex? I take my wife away for the weekend, that's $300-$400. If I'm desperate and end up on a cam site? $80 for an hour or so, easily. Go out to a strip club? Much, much more than that.
I understand, the real value of what you're selling isn't reflected in the PDF price, but if you can actually deliver on what you're promising, guys will be happy to make you rich. The only question is how much I'm going to believe you up front. The more evidence that your stuff works, the higher price I'll pay. Just make sure it's good evidence, not retarded claims - I'm totally desensitised to any claims of miracles or getting laid tonight.
Anonymity: You need the PDF version. I value anonymity very highly. Buying your stuff means I'm admitting: "I fail so hard, I need some other guy's advice to get my own wife into bed with me." I don't want my wife, my family, her family, my non-married friends, etc. to know this. I'm not going to put it on my Kindle (which is shared). I'm not going to have a hardcopy. I bought it with a prepaid credit card I bought with cash at a 7-11 and registered to a fake address. Then I downloaded it and saved it as "overroute_analysis.pdfx". (When I went to your site, the homepage talked about how you were killing the PDF. I found it ironic, because my reaction was "Oh well, to torrents I go then".)
Low price: I'm worried that you plan on dropping your price to 99 cents for the "old" edition. What message is that supposed to send to me? That your content is mostly filler, so that you can just drop the old stuff? If the 2011 gets me laid, why would it stop working in 2012? IMO, that detracts from the evidence that your approach works.
Content: One thing that may work is to split your books up into areas of interest. Make each one $5-$15 (or more, if you can target properly). The girl at CopyHackers.com did this, and it's brilliant. Of course, I bought the whole bundle. But, this allows you to add content without maing the older content look bad. It also allows people to demo it, by trying just one of the specific books.
Guarantee: Testing will show you, but for me, I'd rather believe I'm getting a top-quality product (which in turn is going to raise my confidence and success rate) and pay full price, than just do a "meh, why not" purchase. A money-back guarantee doesn't help me much, but a promise of "Read my book, put it into practise. If by next month, you're not getting at least 20% more sex, then email me and I'm going to help you out." The point is that the PDF is worth that much, and you're so confident, that you'll even answer a few questions if it doesn't work out. Apart from that, you might want to sell your time directly, but I don't think you need to offer a cheap "no time included" PDF version.
Porn: Have you considered doing selected cross-marketing for specific sites? Most porn on the Internet is crap. My wife expressed a bit of interest in watching porn with me. Am I going to go to a free tube site and show her some random "13 guys demean a girl as she pretends to like it" video? Hell no. Consider approaching a few high end sites (e.g. Beautiful Agony (non-nude!), X-Art, and perhaps a high quality couples cam site) and seeing what commissions you can get.
Adverts: On the flip side, a lot of those sites might be able to send good traffic your way. Backpage and the like might also be a good place to find married guys that are rather desperate.
Community: I might be interested in personalised responses to my particular complaints, as someone mentioned here. But anonymity needs to be topmost. I also don't want anything too involved. I definately don't want emails coming in every day regarding new forum content. But, if you can get a community going, I'd pay for access to good summaries of the best content.
I wish you the best luck.