I think if you actually screen who you hire you will find someone who cares about their work, is talented, and will understand you are a start up and charge accordingly.
Because you are asking the designer to do all the work without the guarantee of getting paid. The result is that you get a crappy product, where as if you just bit the bullet and hired a designer you would get something that you could actually use.
I would say just go out and find things you think are particularly well done. Blog about it, what attracted you to that piece, what you dislike. Then go back through it, you'll notice trends. Try to figure out why you react the way you do.
Then once you know what exactly you like and don't like, make stuff.
I think that the first step. Specifics are great too, eswat's recommendation, try to get your hands on Bringhurst's The Elements of Typographic Style. It is the bible for everything type, and is really well written.
I could have actually used this instead of botching my garden by putting everything out too early.
I signed up for the free one, when you get to the calendar view its for the entire year. I would maybe limit that and keep it within three months or even two, so it is immediate, more so then what I am supposed to do next February. I would also, when you click instructions it links you an entirely different page, it would be so much better if it just dropped down there were illustrations in the same style as the home page in an easy 1,2,3 style.
But you should not be scared I think it will definitely catch on. It might be nice to expand it to flowers
I'm currently going through the same thing, its not over but I've realized a couple things
My philosophy is start to do something, if it something you realize is not for you, you cross it off and do the next thing on your list. It doesn't matter what you do as long as you are doing something. For me this has narrowed down and grounded my interests, and has given me an idea of what to do with myself. This idea will obviously change with time, but for right now it is a start.
Or when I feel like I cant think, or am not in control of the way my life is heading. I stop, and simplify my life. whether this is a day to lay in the park and read or just look at the sky. Or something more drastic. It is backing up from your own life and editing it to whatever degree you want. For me it was really empowering to be in a place of my constructing after I threw away all the metaphorical clutter. It let me breathe and start again.