Given that pollarding--the drastic, annual cutting back of branches to the main trunk--is employed on many woody plants, chances are that you could not kill or seriously injure this plant by cutting it back. That's not a guaranty ... just a prediction with high probabilities. But Spring is a better time to do serious cutting. Now, it'd be best to limit cutting to just what will solve the window-covering problem. (Hard cutting produces lots of tender replacement growth which is not what you want if potential freezing is just around the corner. Foliage needs some time to "harden off" before frosts.) In the springtime, everyone knows how foliage seems to suddenly burst out of dormant plants. Just before this happens is a great time to do major pruning. This allows a plant's stored energy to be put to best use ... growth where one wants it. In this case you might decide on the height you like. Determine (from past observation) how much height this plant will add when it takes the "leap" during the growing season. Deduct that amount from the desired height (in anticipation of new growth) and cut it there. If the plant is a rampant grower, this will be a drastic cut. If it's a modest grower, it will be a more reasonable amount. Part of this equation also depends on how many times a year you are willing to cut. Factor in height removed with the number of intervals of pruning. Cutting in ANTICIPATION of growth is my preference; it has some advantages over cutting in REACTION to growth. Chances are good that this is NOT a dwarf Lorapetalum (if indeed that's what it is) like you need, but instead, one of the big fatties that make nice, small trees. You might consider replacing it with something better suited, or get used to hard pruning or that which is constant and ongoing.

You can cut back to the graft (if it's grafted) or to the root ball. This winter was very hard on my roses and even after pruning off what I thought was all the dead stuff, I would see new brown and black on canes that looked healthy before. Just keep cutting back until you see white pith (the filling in side the cane. Anything brown or black or reddish should come off. Roses are very resilient. Some that I cut down to nothing a few weeks ago pumped out new growth and have buds already.

cootie- A question. Will the contractor be rolling back and forth over the bamboo, or is he just concerned about lowering the clearance. The reason I ask is that, if you don't have to cut the culms all the way to the ground and can leave some stubs with leaf mass, then the bamboo will be able to regenerate faster. On the other hand, If it were me, I'd be digging up rootballs and heeling them over in a pile of topsoil, and then replanting them after the contractor was done. But, digging up divisions of mature bamboo (and not killing them in the process) is hard work unless you have someone who is experienced in doing this. Unfortunately, you're about 1000 miles away so I can't be much help there!

If it's an evergreen, (indica) go back to where the new wood comes from the old. There are usually plenty of dormant buds in this area. Make your cut about a centimetre into the new wood side and keep any leaves in the area. You'll need to keep it shaded until about May next year, and misted, or covered with a damp light cloth to protect it from water-loss. If it is a deciduous azalea, they do come back from old wood, a bit like several Rhododendrons, but it can take a couple of years after being moved for them to feel settled in enough to do this. They take AGES to re-establish roots beyond the ball you transplanted and need all the mulch, wind protection, and spare water to keep the root ball moist (not wet) you can manage - especially over the summer. If you're transplanting into a shady gully that's reasonably moist/sheltered you can probably skip the fussing. I did the fussing for a 2m mollis in the middle of a dry spell and it lived to both tell the tale and flower cheerfully. The last evergreen I moved was at the beginning of winter, so I didn't need to fuss beyond putting a big rock on the root ball to stop it lifting in the wind.