It basically comes down to your unique situation and what your expectations are. I have a pretty tall house, Victorian Farm Style. I run my GMRS antenna in the attic which is about 3 stories off the ground. I get very good performance.
My system performance is almost completely dictated by topography. Utilizing RF propagation modeling and line of sight calculators I found moving my antenna up, even quite a bit higher, will not make much of a difference. So in other words, moving it outside just isn't worth my time or money as its performing as I expect it to.
If I had a one story ranch I would likely feel differently and try to wring out every bit of performance by moving it higher and outside.