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I'd go with Under the Bushes Under the Stars, I love that album. Propeller is pretty good so is King Shit and The Golden Boys. Then you could go ahead and listen to their later, non lo-fi stuff if you're so inclined. Mag Earwhig, Isolation Drills, Earthquake Glue, etc... They aren't perfect, but there's good (and catchy) songs on all.
Robert Pollard's solo stuff is kinda hit and miss. The guy puts out soooo much stuff that sometimes you've gotta wade through the crap to find the real gems. I really liked From a Compound Eye, that's not a bad place to start with his solo material. Robert Pollard is Off To Business was decent too. It's really straight forward, but not bad.
Pollard's new band (Boston Spaceships) just put out their first album, which I haven't yet heard.
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