I might leave the crepe Myrtles alone for now. CMs are pretty hideous in the winter, but you may love them once they bloom out!

Do you need the pool fencing up?

Hi Lindsay, The fence is removable but we keep it up most of the time because we have a 4 and 6 year old that are still learning to swim. We are looking forward to the date when we can retire the fence for sure!

I don't mind crepe myrtles typically, but I feel like these look unkept. They are so large now that I'm not sure how to prune them without making them look butchered. They also drop leaves, blooms, etc. in the pool all year long so they have been a bit of a hassle to deal with.

The information shown in the panorama is too shrunken and distant. The other pictures are piecemeal so I'm afraid that's all that the feedback can be. If you want more comprehensive feedback, you'd need to take a series of sequential, slightly overlapping pictures that show a whole scene from end to end (like from the outbuilding all the way to the house). It would show all the potential landscape space in between. To do it, you'd probably need to stand at the pool deck (not far from gate and not far from the portion of the yard you're capturing and roughly in line with the scene center) and capture the entire area contained within the yard perimeter fence. The camera would stay in ONE spot and pivot, taking slightly overlapping shots, to capture successive pictures.

Looking at this picture, we can see that it would be useful to have the roofs of distant buildings screened. If you committed to pollarding the crapes, they could pretty much accomplish this goal, all while keeping healthier looking foliage, massive flower trusses and a "bouquet" appearance which I think suits being around a pool better than the rangey/woodsey look. I acknowledge that there are plenty enough bad examples of crape cutting to warrant using the words "murder" or "butcher." But this is easily avoidable while bringing some distinct advantages. For one, it controls the size and creates a handsome trunk/canopy relationship. Two, it increases leaf and flower size; and 3, leaves look healthier and are much longer lasting on the plant. Flowers grow into enormous trusses. Personally, I love the way they grow on long, arching canes that makes the tree look almost like a weeping tree. Cut them straight across the top, not like a single-dip sugar cone. 9' above grade is a good minimum height to cut for a residential yard. The canopy will return to slightly lower than that, still allowing a person to walk below without getting scraped in the head by branches. Be aware that the canopy fullness is not instant on newly pollarded crapes. it takes a couple years to develop and continues to get better every year. If you don't like the narrowness and stiff verticality of the existing trunk structure, chainsaw it to 8" above grade and start completely over. A new form will be there by summer's end. Personally, I like them to be slightly wide-spreading. 45* - 55*.

It would seem better to me if the outside of the yard were surrounded by a perimeter bed next to the wood fence/and a smaller lawn. Not using this picture to say what should be in the bed, Just that it is a bed.