Wil,
I prefer the roller wheel to a tape for the very reason that the handle extends to 6' so that I don't have to get behind bushes, etc., or climb over the hill of snow that fell from the eaves ..
Have been known to carry cross-country skis with me, depending on recency of snow fall ..
Have removable short riding chaps .. velcro holdings .. that extend my shoes up to my knees for walking in loose, deeper snow. Easily removed when done, and keeps snow from getting into my sneakers ..
On occasion have resorted to inside measurements (with the wheel) when the exterior is difficult .. eg., hillside, etc. ..
Finally, been known to count the concrete blocks in the foundation, or the number of divisions in board & batten, or the number of 4' pieces of T1-11 .. whatever removes the exterior from the feline ..