BED all day long so long as time to the meeting/event is not the problem. Getting in to BOS usually isn't a major problem. It is the outbound that usually gets us the most delays. Heck, BED is worth it just to keep from going through the security screening at BOS.
Depending on what size plane OWD might do your trick. Close enough to the city (same as BED) but with three ways to go. Either mass pike, through dedham, or up 93.
Depending on what time you get there it could literally be 2 hrs to get into the city. If you're talking outside the city it could be a lot less. But i've seen traffic backed up on the mass pike for 10 miles and not moving a foot.
One thing you're not factoring in.
The cost of a limo ride into town from BED versus the landing fees at BOS. They are about the same. A cab ride from signature boston is about 13 bucks into and 19 coming out. With tip.
A limo with a wait will cost you far more than the landing fees of a midsize jet.
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