The picture of Actinidia kolomikta (hardy kiwi vine) below is the after shot in a 3-year game of musical chairs in the garden. When I first started gardening, every time I moved a plant, I would dwell on the idea that I had made a mistake. Now that I have moved, oh, say every other tree, shrub, and perennial in my yard about 3 times, I have come to a few practical conclusions.
Conclusion one: sketching things out, even in a very rough bubble-looking form of where, what, and how you want things to look, helps minimize future digging games. If you know you would like a patio in a certain area and you block it out in a sketch, you most likely wouldn't plant a grove of spruce trees in that spot by mistake. Get out those pencils and paper, class!
Conclusion two: read the tag for size (please, please!). This is most often a problem with trees. If that "cute as a button" little 5-foot tree you planted 10 feet off the front door of the house gets to be a 30-foot wide behemoth, goodbye all sunlight in the front room. And any visitors for that matter. How could they get to the front door?
In general, I find the width measurements more important than the height measurements for trees and shrubs. Unless you are planting under a utility line. Also, I don't plant any trees closer than 20 feet to my house at a minimum (and these are usually narrow or dwarf varieties that won't eat up space). Many of the house lots in developed now in Anchorage are relatively small, so I often recommend varieties that don't get very wide. One tree that is tall and narrow, for those tight spaces, is Populous tremula 'Erecta' (which says on the tag 40' x 6'). Yeah, I know, it's a poplar. But you can't get much narrower than that in a tree up here. Other small trees include some of the crabapples (Malus spp.), serviceberries (Amelanchier spp.), and some mountain ash, such as Sorbus decora. Go ahead, snoop around, visit nurseries, read magazines, surf online. Find something that fits and will still fit in ten years or twenty.
Conclusion three: read the tag for cultural requirements! Does it like sun? shade? wet soils? being trampled by the neighborhood children? Putting the plant in a place it will be healthy also minimizes those annoying musical chairs games.
Conclusion four: even if you have planned for every contingency, requirement, and eye appeal, you may decide you just don't like that plant in that place. Don't feel too bad. Mixing things up occasionally keeps the garden fresh and interesting, so go ahead and plan your moving projects now. When spring fever hits, you'll know where to dig.
Disclaimer: If the plant you want to move (or remove) could possibly fall onto your neighbor's yard, your home, overhead wires (in other words, if it's anything bigger than say, 8 feet), an arborist would probably be a better option than a DIY project.
The before musical chairs picture, a mishmash of Rosa 'William Baffin', Rosa 'Pole Star', and Actinidia kolomikta, all fighting for vertical space against the house. What a mess. Nothing a little digging won't fix, though. If you decide you are willing to part with plants you have dug up, consider sharing with a friend or neighbor (or put them on Alaskaslist). These days, I prefer to think of moving plants around as an opportunity (so long as my back holds up). So should you.