Help structuring blog archives and background in transfer from standard html web

I am looking to turn this site into a WordPress blog. Currently it is just a regular html web page, but it’s pretty klunky to update. I would love to be able to update it using WordPress with the added functionality of sending out automatic Tweets and Facebook updates in one simplified process.

Here’s what I WANT to do – can someone please tell IF it is possible and give some tips on HOW to do it.

I know that I can create a static home page. I read instructions on how to do that and can find them again easily enough. Am I able to maintain the current structure of my site with individual archive pages that consist of 365 days but NOT the regular calendar year and assign a different background image to each archive?

You may need to look at my current site to grasp what I am asking. But in a nutshell, it is a collection of comments from my daughter as a 3 year old and as a 4 year old (and will soon feature her as a 5 year old). So I need archives (if it is even possible to split them up) to cycle on her birthday rather than on January 1. Also, my page backgrounds come from some artwork drawing that she did at some point during that year in her life, so I would want each archive to have its own background rather than a standard background for the entire blog.

Then, in addition to the archives, I would add another page for current posts to accumulate. I would also add a frame on the front page that displays just the most recent new posts – I think I read somewhere about how to do that.

Lastly, I would like to add a pre-fabricated theme to make it look better than the dull formatting of the current page. Maybe add a child-like font – but nothing too detailed so that I can keep her own drawings as the primary background. (On my current page I’ve tried to select the least obtrusive drawings so to not interfere with reading the actual web page text).

Is this too tall of an order? Hopefully not…

Thanks for any help!