What's the best way to go?

Originally, Brad and I had planned this summer's vacation to be a tour of East Coast baseball stadiums. We were going to start in D.C. and travel north with stops in Baltimore, Philadelphia, New York and Boston. Upon further discussion, we realized that the price for this plan would be astronomical. Plus, we did a lot of moving around during last summer's trip and it got to be tiring.

After considering numerous options, we decided instead to head to Las Vegas for a week and then fly to New York and stay with Brad's mom for about 2 weeks. We love Vegas and you can't get much cheaper than mooching off of Brad's mom. :-) (She was, of course, consulted and approved this plan.) Being in New York, we'd still be able to do at least one baseball game. We're also planning to go to Philadelphia for a day trip and hope to catch a game there, too.

Now comes the hard part: Plane tickets. All of the airlines offer multi-city itineraries, so there will be no backtracking to Vegas. The problem will be picking the right one. Three airlines currently offer the least expensive fares — all within $50 of one another.

Option #1 is automatically thrown out because I hate that airline — it loses our reservations, it loses our luggage, it hires people with no customer service skills and its planes are uber cramped. It is also the only airline known to frustrate Brad to the point where he shouts inappropriate airport phrases in the middle of an airport. (I admit that was partially my fault. I was not helping the situation.) So we try to avoid that airline.

Option #2 is my favorite airline but, unless I want to pay a lot more, it can't get us from here to Vegas without a 12-hour layover or a connection in Chicago. Chicago? Also, its only nonstop from Vegas to JFK leaves at 7 a.m. Anyone that knows me knows that I don't do 7 a.m. — especially if I'm in Vegas. I could do a one-stop itinerary, but that would take us from Vegas to LA to JFK. Seems like we'd be going the wrong way before we went the right way.

That leaves me with Option #3. It gets us to Vegas in a minimum of eight hours. (More if I want a longer layover, but who wants to spend time in Phoenix?) It offers 2 nonstops from Vegas to JFK. I'd prefer to leave at like 11 a.m., but this airline offers 4:30 p.m. (which lands in N.Y. right after midnight) or the red-eye, which leaves Vegas at midnight.

Hmmmm. What to do? Recommendations?