I appreciate the responses and I see the concerns. It sounded like most of the problem would be fall risk. To address that, I made the little sketch below that shows where I want to put the trees. They would be right at the property line which opposite my house has a steep dropoff away from my house. Also, my house is probably 40 feet high at the peak on side. that should mean that most of the weight of the tree would be on the opposite side, much of it overhanging the big slope away from the house. Since the house is a good half as tall as the trees will ever get, the green in my photo should be scale to the most that ever might over hang my roof. I can see that there would still be some risk, but wouldn't these things reduce the risk considerably? And since nobody addressed the root question, does that mean it would not be an issue?

Only a fool would plant crepe myrtles near a pool -- and the PO of my home was a fool! ;-) I have 4 of them across the end of my pool. My neighbor had them near a pool at a previous home and said never again, but we are living with ours. They will create some more work for you. The problem is having a gazillion blooms followed by a gazillion seed pods and another gazillion or more seeds -- as well as tiny twigs and branches, sometimes strips of bark that peel off and can blow in. It's just a more high maintenance cleaning issue, and I have been known to put pantyhose over the skimmer baskets to trap those darned seeds and tiny twigs. Since we weren't the original builders of the pool, I don't know for sure if the filter grids we had to replace were due solely to age or if some fine twigs got through and made holes. I didn't want to find out the expensive way. Mostly -- it's just the blooms and seeds and a lot of basket cleaning. It's all I know, and they are pretty, so I deal with them. I don't plan to take them out unless they are dead or causing damage, but I would say consider the most common wind direction in the summer (blows into our pool, so across the street they might not be such a pain) and your proposed placement and suggest that you don't plant a line of them. They might be worth it to you. Just know what you are getting.

I'm in Hopkinsville, in southwestern KY, about 1 1/2 hours from Nashville (we're northwest of it). We're 6B. Crepe myrtles are fairly common around here, but at least small to medium-sized ones an get killed back to the ground if we get an extreme cold snap. For example, we get down to the teens for lows occasionally, once in awhile might hit zero, but a couple of years back we had one night with an anticipated low of -9 to -11 degrees. That killed a young peach tree I'd planted the prior spring, and (I think that's what did this) busted the trunk of a beautiful young Bloodgood Japanese maple I had at a place I work (it put back from the roots; I let the suckers grow one year, then this spring picked one & cut the rest). My point is, if I'm 6B and you're aways south of me, you may be '7A' or what have you, but even up here, we have crepe myrtles. I've got a pink velour in the backyard at home - which got killed to the ground & put back out from that same winter. This year, not so bad, wasn't killed to the ground. Richard.

I may be repeating myself, but keep in mind that we're not working with an ideal situation. The windows are too close together to squeeze a tree in front of and between them without it seeming as if it was a wedge pounded into a crack. Nevertheless, the scene can be improved by improving the maintenance (trimming.) I would definitely remove the end shrubs. Having them exceed the wall length looks like someone didn't "cut the trim the right length." It is as if a baseboard were longer than the wall it was attached to. You don't need to cut the hollies lower so long as you have them a little lower than the finished product, and it looks like they are. Keep in mind, since they are a plant that will grow substantially larger than the space allotted for them (the space below the windows), the only practical way to finish them is with continued shearing. Basically, you will be sculpting a hedge with hedge-trimmers and then sculpting it again every time it puts out a few inches of new growth. There are too many conditions working against you to maintain it as a natural finish hedge with a looser look. You have the option to cut the shoulders of the hedge crispy "square" or rounded. Either way looks good though each creates its distinct flavor. You'd want to coordinate this flavor throughout the foundation planting and not mix it up. Another feature of properly trimmed shrubs/hedges is that their side will slope outward so that they are widest at the bottom. They can be straight, but this neither looks as good or lets the bottom of them receive as much light. They can never be trimmed so that the bottom is narrower than the top (which is how almost everyone does it!!!) because they will lose their bottom foliage, due to it being shaded, and become bare at the bottom, as if a hedge or shrub on stilts, which is very ugly. Without question, you must clean up the canopy of the crape myrtle by cutting off all branches and foliage which hang down below a certain line. Usually, this would be over one's head. If the foliage is hanging down below the windows (including a few inches of clearance) then the arbitrary line at which it was cut is too low. I'm not talking about cutting the crape at the top, but removing what hangs down below the red dashed line. It would look a bunch tidier and more organized to clean this up. If you are pollarding the crapes every year, a good height above grade at which to cut their tops prior to early spring, is 9'. A given situation might call for a different measurement, but 9' is a good average. After the new top grows it will hang down a little below this, leaving and 8' ceiling, which will work for most situations. If you want to add more interest with a flowering or colored foliage perennial that is lower than the hedge, place it at the ends of the hedges/shrubs, not in front of them. Let it protrude forward of the hedges. Then fill in the foreground solid with a lower groundcover. You already have the Liriope. I'd just split that up and redistribute it over the whole area ... solid, not as a cute edging.