Yeah Ben, my feeling is you're spreading yourself really thin. Both in terms of what you are offering and where. I would sit down and figure out where and on what you make the most most money and focus on that. When you get that working continue to hone it and add something else.
I actually wouldn't be too hard on the web guy, he sounds like a standard web guy. He will give you what you ask for and they tend not to say 'no that won't work' because a) they want your money and b) they are not usually that savvy to what works and what doesn't, they just know they got paid.