I wanted to add something to your ideas about turning your game developement into a full time job using a business model based on online comics. Sorry that I'm a bit late with this, but my timetable was a bit crowded the past weeks.
Honestly, I don't think it would work. Or at least not particularly well.
Some of the problems have already been mentioned by others, like the problem of sex being a bit of a no go in many social environments. And this applies even more so for hentai and furthermore for hentai games.
This is just the most pressing point that would limit the purchase of merchandise from a game like yours.
There are some other things I'd like to point out. On your blog the "Chaotic Neutral, bitches!" quote for a coffee mug was mentioned as an example. I'm aware this was only an example, but it illustrates two additional problems you would encounter.
One would be "offensive language" which again is not entirely appreciated in many social circles, so we hit a bump along the lines of the general hentai problem.
The other: If I saw someone with a mug like that, I would never assume it to stem from your game. I would assume her/him to be a hardcore DnD fan.
A lot of the humor in your game for example is based on working with clichés. Anybody seeing merchandise of your game would think about the cliché and never even bother to investigate, where the particular merchandise comes from.
A part of the whole merchandise idea from webcomics is, that the merchandise in itself works as advertisement. Which in your case most of it probably wouldn't do.
Another factor is a psychological trap people would probably find themselves in with your game in comparison to a webcomic. A webcomic is an ongoing process, which feels like "we're going somewhere".
A vidoe game in developement is an ongoing process as well, but the associated feeling for most people is "only half done".
It's a variant of the cup half full/half empty problem. People feel more inclined towards half full and thus the support for "half full " will be better, even if you could manage to generate the same amount of interest popular webcomics get.
A finished vidoegame might have better chances in that respct, but a finished video game doesn't get that many site hits after people got the product unless you're constantly providing additional download content to integrate in the game. (A workaraound on that problem might be to create a wiki for the game and advertise the merchandise there. But I'm honestly not entirrely sure how well that would work.)
I had a third point, but my new fridge came halfway through the post, and I stupidly forgot somehow. Damn you, mesh brain...
If I can remember what it was, I'll edit my post accordingly.
If you stumble across any typos, you may keep them and rear new ones in your basement.