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Well, getting away from the lead debate for a second.
I've been thinking about this some more, and if your wood is really bad, you should focus on making weather tight repairs first. Don't forget the windows. The wood really should be as clean as possible before priming. I used Valspar "Duramax" and had great results. It was sort of a satin color.
I also used an airless Wagner paint gun because the siding was the sort that a roller wouldn't cover everything. The airless gun required the paint to be thinned out a bit or it would clog. It also does not have the type of adjustable fan tip that a pro gun has. I would probably look into renting a professional sprayer.
Also, I would recommend looking into elastomeric paint since your wood is old, not new. And it may move around a bit, which is why your old paint didn't last.
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