L.A. to NYC in January road trip, need help planning.

Hey guys, my first time posting here.

I have some general questions that some of you might help me with.
Me and 2 friends are planning a road trip from west to east in January, and we would like some more info on some of the thoughts we've been having for the road trip.

So we'd arrive in San diego from europe, but wouldn't start the actual road trip untill we're in LA. We were thinking about following the old route 66 for a bit before turning off.
Basically, here's what we had planned:
LA-Las Vegas-Grand Canyon/Flagstaff-Dallas-New Orleans-Memphis-Chicago-Pittsburgh-Washington DC-Philly and end in NYC. We're planning on using around a week and a half on the trip.
So my first question is , how sensible is this route? I figure i picked a good one based on weather, scenery, big cities and trying to get as much in to the trip as we can.
Our main concern is the car. We are not sure wether to rent one way, or to rent a few times, maybe LA to New Orleans and from NO To NYC, or Chicago as the middle stop, we're not sure.
Ive seen the big ones pricing it from anywhere between 1300 total to 2500 total for economy-standard cars. They offer the car for 90 a week but then add a 1000 dollar drop charge, and a one way fee on top of it sometimes. Its a jungle, so i would appreciate it if anyone who had some experience in renting cars for long distances could guide me through it.
Also, since its January, we wanted to go as south as possible to avoid any potential snow storms and icy roads. We're clearly thinking this could be a problem once we go further north than Memphis, but we have many friends in Chicago we'd love to see. The alternative would be to go through atlanta and up the coast, but then we'd miss chicago and memphis among other things, and we'd like to see both.

FYI, last year in January, we went across the country too, but that was by plane, LA-Vegas-NYC-SFO-San Diego, in 2 weeks, stopping for a few days in each city. This time were really just planning on stopping by for a few hours before heading on, so i'm thinking 1½ weeks for a 6200 km road trip should be enough. We might even be faster.

So yea, anyone who can help me out in anyway with some info on anything? Ive only rented a car from San Diego to LA before, so i dont know how it works long distance. Also, the driver is 25.

Thank you.

Hello and welcome to R.T.A.

First off, I can't imagine hiring several one way drop off cars would be cheaper than doing this just the once, especially as you aren't going to be in one place for long where you might not need a car for a few days, but there is no harm in doing your homework and pricing it up.

Your trip is doable but looking in the region of 4000 miles over 10 days you are going to spend a lot of the time behind the wheel, and by trying to "get in as much as you can" you are not going to have much time to take things in, but you already know that.