We have a rather complicated trip that needs some figuring out:
We will be flying into Boston from San Francisco. The only piece set in stone is tickets to a weekend of music @ Tanglewood MA. - Eastern MA. Listed now are the other places we would need to figure out getting to. We will drive to Tanglewood but do not want to spend hours and days in a car so we are OK driving back to Boston and from there??
1)Cape Cod (Welfleet) - could take "Cape Air" OR drive.
2)New York State (Buffalo) (Jet Blue)
3)New York State - Livingston Manor (Catskills) drive??
These 3 destinations are places where we have close friends whom we want to see. We are willing to fly to Buffalo - then back to Boston... etc.. Hard to figure out Catskills as it looks as if we'd need to drive there... OR we could fly Buffalo > Albany and then rent a car and drive Albany to Livingston Manor.. THEN take the car back to Albany and fly to Boston??
HELP!

You don't say when but do check the Saratoga Races as many fly into Albany and car rental during the races is very high.

I like to use google maps to figure driving distances. Tanglewood is in western MA not eastern so I would drive from Tanglewood to Livingston Manor. (2 1/2 hours approx) then Livingston Manor to Buffalo (approx 4 1/2 hours). One way car rental.
Fly Buffalo to Boston.
Fly Boston to Welfleet?

Tip for long drives: find a half way point for a meal or interesting town or museum to explore.

The plan dfrostnh has given you is about as efficient as you can get as long as the drop fees for the car are not too bad. of course the Wellfleet part could be done at the beginning go the trip, before you go to Tanglewood either by plane or by car, if that would work for the total trip.

Also, make sure you understand toll roads. Ma has the no pay toll roads now. Rental car will charge you toll and convenience fee.

I agree, the plan dfrostnh has given you is about efficient as you can get. I'm sure our resident "you should take the train everywhere even if it takes 3x as much time" guy will chime in...
In this case train from Buffalo to Albany may not be a bad idea if you don't want to drive.

Personally, I'd rent a car in Buffalo and return it in Boston. Definitely heed what macross is telling you about MA toll roads. I have an EZPass transponder in my car so I don't have any clue how it works with rental cars. The only practical way to traverse MA from Boston to Tanglewood, or NY to Boston is on the toll road Mass Pike.

Good point J62 it might be less expensive to do the trip in the reverse direction, but do check the costs each way.

The problem with taking the train to either Albany or Schenectady is that there are no car rentals located at either station so you'd need to take a taxi to get to one and that will add time & cost.

FYI,
The New England part of the trip is not complicated. It's the New York part (which is NOT part of New England....) which is.

Do you already have tickets SF to Boston? I probably would have flown SF to Buffalo, then drive the 4 hours to Livingston and then 2.5 hours to Tanglewood. Long drives but driving an hour to an airport, getting there 90 mins early and then flying 90 mins is no quick hop either, and the drives are more interesting. Car rentals one-way out of Buffalo don't look prohibitive but that would depend on time of year etc.

Note that Cape Air flies out of White Plains which would be less than 2 hours drive from Livingston, if for some reason your plans end up putting you in Livingston before you head to the Cape. Also they fly out of Rutland VT which is a beautiful 2 hour drive from Lenox- instead of backtracking back into Boston traffic.

Maybe let us know a little more about what exactly is set in stone......dates available....if you're already in Boston on a certain date as well as Tanglewood etc? The way I'm understanding in you're flying into Boston for sure, going to Tanglewood for sure from there....and then want to figure out how to fit in the rest which will be AFTER Boston and Tanglewood?

set in stone is tickets to a weekend of music @ Tanglewood MA. - Eastern MA.

Tanglewood is in western Mass (Lenox)

oops... sorry i see someone already made that correction

I would forget about flying between any of these locations; by the time you allow for airport time it would be faster to drive - with the exception of perhaps BUF-BOS. A variant of dfrost's itinerary. Fly to Buffalo (if you have never seen Niagara Falls and have time, see that while in general area). Rent a 1-way car. Drive to Catskills (4.5 hours, approx). Drive to Tanglewood (2.5 hours). Drive to Wellfleet (4 hours). Fly back to SF out of either Providence, RI or Boston. I know you don't want to spend a lot of time in the car, but much of these routes are reasonably scenic with some interesting stops possible. Lenox/Tanglewood to Boston if about 2 hours, but you must add concert exit traffic to that trip. This way you never spend more than a half day in the car at a time.