Truck has a 2.5" leveling kit, otherwise stock with 265/75/16 tires (with stock rims).
A couple questions:

1. Using the stock rims, can I go bigger with no (or minimal) rubbing - such as a 295 tire or ....what size?

2. Does anyone know how big of a matching spare will still fit in it's stock location (I'd like to have a spare!) ?

3. What is the better choice - going with the 265, 285, 295 type sizing or going with the 33, 35" sizing? Is there a difference, pros or cons? I do mild off roading but do drive quite a bit in snow/ice/winter conditions.

 

You could easily put 35's on your truck if it has a 2.5" leveling kit on stock rims

 

IMO a 35" inch tire with a leveling kits is to much tire. I would say a 285/75 R 16 which is close to a 32-33 inch tire.