I started with my blog, http://www.southerncrosses.com which I had someone construct for me. I started learning the basics and goofed here and there, but got a little better at it.
I'm not a computer guy...
Then I had help with my next newest site for US military only. (my contribution for the troops) This site just went up and was my first experience with ClassiPress.
With the milswap site I had a hosting site that gave me one more URL so, being an avid sailor, I thought I would strike out on my own and try a ClassiPress site with NO PAID help.
With every glitch I learn a little more. Right now I'm having problems with WP Super Cache on the older Southerncrosses site, but hope to have that solved soon.
So far so good. I'm learning a lot here from forums and professional training sites.
Thanks to everyone that has given me help along the way. And if you have a suggestion.... I'm always open for improvement!