Dentist

My boyfriend needs major dental work and no insurance.  We've been looking into all kinds of different plans and discount plans and insurance and all that.  Basically he was never to the dentist as a kid and needs all his teeth pulled and either dentures or implants.  So I have several questions and am hoping someone can offer me some advice.

When you get teeth pulled they probably wont do it all at once so how does that work?  all top first then all bottom?  or all the back then all the front?  And how long after they're pulled does he have to wait to get dentures.  His biggest concern is walking around with no teeth.  They're ok looking in the front but are absessed(spelling?) and rotten in the back and the front will not be saved but dont look too bad now.  anyway anyone ever been through this or know anything about it?

And whats the best kind of plan to get i know there are waiting plans and premiums and all that so I need to get one that will help pay for some of the extractions(oral surgeon that he'll need because its down to his roots) and the dentures or implants.

Any info will help.