Just finished a play-through, siding with the NCR.

The NCR approached me when I first left the lucky 38, so I chose their quest line. I never did confront Benny or get the chip back, but did that even matter?
Neither Benny, the chip or House were mentioned in the end slides.

Another thing, I never met or confronted Caesar, the end boss was one of his flunkies with a strange mask. Again did that really matter I didn't meet him or put an end to his reign personally?

I think I only encountered 1 small Legion camp in the play through, where the powder ganger hostages were being held.

If I sided with the Legion next time, and assuming the vast majority of the locations are NCR factions, Im guessing there will be a lot of fighting involved and much much less quests to do?

A Ceaser's Legion playthru of the game is both similar and distinct from an NCR playthru at the same time. Many of the Main Quest missions for the two factions are similar and/or the opposite path of the same quest, but there are unique quests for both sides that don't appear at all for the other faction so it's not an exact mirror image. Worth a run thru of the game for each faction just to see the new quests as well as see old ones from the other side.

The Legion path is generally agreed upon to be the shorter one as there are less over all CL-focused quests than ones that are NCR-focused, how you handle each one determines how much more/less combat you'll have.

From my impression, I'm guessing most of the companions would also object to the player siding with the legion? Either by high legion fame or bad karma.

If making New Vegas independent (either with or without house) would that require going against both the legion and NCR?

It's better that you didn't follow up on the other questlines after the NCR offer , it clouds things and you can end up getting everyone ticked off at you .

You can find Caesar's fort by way of Cottonwood Cove and on that count, you missed out on one of the best battle sequences in the game.

I guess it's worth it to play for Caesar once , just to see how it plays out, make sure to pick up the Lucky Shades from the legion safehouse.

By not directly attacking it while allied to the NCR or as an ally of the legion?

I guess clarity isn't my strong point , but attacking Caesar and his goons while attempting to ally with him wouldn't make much sense.

I recommend taking Boone. It's a better battle than the dam in my opinion and usually lasts longer .

If you have a save before the point of commitment at the end of For The Republic Pt. 2 , load it and head to Cottonwood. You might also want to visit with Benny at the Tops.

Don't forget the side quest's though!