I agree with mjv - there's no real easy and quick answer to this - it's a balancing act.
In general, fewer but wider indices are preferable over lots of narrower ones, and covering indices (with include fields) are preferable over having to do a bookmark lookup - but that's just generalizations, and those are generally speaking wrong :-)
You really can't do much more than test and measure:
- measure your performance in the areas of interest
- then add your wide and covering index
- measure again and see if you a) get a speedup on certain operations, and b) the remaining performance doesn't suffer too much
All the guessing and trying to figure out really doesn't help - measure, do it, measure again, compare the results. That's really all you can do.