Personally, I will not enable HTML for anyone on my forum.
But, yes you can do that.
Set registered users to not allow HTML and then set up a promotions in ACP to promote them to a user group that does have HTML enabled after 20 posts.
Other subject;
How do you think it will 'screw up' your style? When I upgraded from 3.5.4 to 3.6.0 I just had to revert and re-edit my templates. No biggie.
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