Having not read your HN profile (one of the best we have here, incidentally) since you added this site back in, it took me a moment to reconcile your real name with your handle - kind of a Wizard of Oz moment for someone who has been appreciative of your many contributions on HN over the years.
Enough of an aside, back to LearninFreedom.
Yes, it is a little old-fashioned. I couldn't have done better mind you - the key items I notice that make it feel that way are:
1) The site logo. There may be a great history behind it[1]. It does look like 13 year-old MS Paint with two different fonts (incl the TM). Could be 'streamlined' and would immediately add fresh impact. (This also goes for the favicon).
2) On my laptop (19 inch widescreen, running Windows 7, FF 18.0.1) the body of the website is left aligned and leaves almost a third of my screen on the right hand side as white space. My (non-technical) observation of other sites (including ones I've worked on [2]) are that they tend toward centering the content so widescreen users get some whitespace either side, which I also find aids readability.
So my mind sees 'centered content' as more recent, and therefore your site as 'older'.
3) It wasn't clear to me initially who your audience was and what 'Learn in Freedom'(TM) actually meant. It may be common terminology in your target audience, so don't force a change because of me; at first I interpreted "taking responsibility for your own learning" to mean life-long learning, eg Khan Academy, adults using the local library.
Later it became clearer this was more about Homeschooling - is that correct? Is it also supplemental homeschooling - ie, teaching your kids other things while still mainstreaming them[3]?
So the introduction could perhaps have better explained what 'Learn in Freedom' means and who the site is built for.
4) Usability point - the site would benefit from a clearer content structure. The content, listed in A-Z, is also broken down into a few headings on the homepage and categories / subcategories in the site map.
These could be made clearer, so as to make the content more digestible. Other categories could be "Getting started", "Where to ask for Help", "Supplemental v Full Time", "Curriculum / Lesson Ideas" etc (again - I'm not specifically your audience, these are just the things I would be interested if I was starting down this road. Experiencing homeschoolers would likely see a different structure to the content).
=
It almost ... almost ... goes without saying - thanks for sharing, and putting the site out there for open feedback. How fabulous that it was a post from a 17 year old that compelled our tokenadult to do so.
=
[1] Eg, 'This logo was created by one of my children in 1999 when they first started using computers to learn from home'. If it's a great story, maybe that could be mentioned (eg, as a mouseover).
[2] See http://everydaydreamholiday.com and http://www.shirlawscoaching.co.uk/ , not as examples of beautiful sites but rather to my point about whitespace and centering. Both were built out of templates (Wordpress and Squarespace respectively).
[3]If so, it's a topic I'm fascinated by, though not ready for yet (absence of actual children being my main roadblock). To that extent, I found the home page excellent in regards contents and wealth of links (which I haven't followed, however). I can't really comment on updating the content or direct you to other bodies of knowledge in this field, but I feel better for having reviewed the site and thought some more about my future options as a (future) parent.