Newbie needs advice

Hi All,
If there is someone who could give me a bit of info, I sure would appreciate it.

I've been trying to set up a blog on Geo & Chevy Trackers and Suzuki Sidekicks that you can see @ http://www.tracker-sidekickhq.com. With all the publicity out there on the web, etc. I started out with Wordpress and managed to get set up, although I still have a lot of work to do. At first glance, WP seems fairly intuitive, but I've now reached a point where I'm wondering if that was the right decision.

Before going further into the blog set up, I decided to check out Drupal, so have been looking around the site and forums. I gotta say that all the info & technical language has got my head spinning to the point where I seem to be going round in circles, and finding things intimidating.

My questions are the following:

- Is it possible for someone who has limited techie knowledge to get started using Drupal within a reasonable time frame?
- What advantages are there to using Drupal?
On a more specific note, I would like to have a photo gallery where registered users can upload photos with captions or comments. Is it possible to do this within Drupal?

Also, after reading a fair bit, and while being fully aware that each system has its own techno-speak and buzz words, I can't help but wonder I'm too technically illiterate to be able to use Drupal.

Any help would be really appreciated 'cause I'm kinda overwhelmed right now. :-[