Markdown & SmartyPants with WP

I’m redesigning my site and considering moving from Movable Type to WP, but many of my entries are in Markdown. I really, really like Markdown and SmartyPants. I’ve not used Textile much, but Markdown feels more natural to me; also, I love SmartyPants because I’m a stickler for curly quotes.

I understand there’s a Markdown plugin for WP, but I have two questions:

1) My “links” entries (automated posts from del.icio.us) are in HTML format. My written entries are in Markdown. Can I specify a default (say, HTML) and then make an individual post (i.e., when I start a written entry) Markdown?

2) Is SmartyPants or an analog available for WP?