I've moved house a fair few times recently which is great because each time I've moved house I've got a great looking garden! Maybe you could do the same with your LMS and be happy :) Just like moving house, the downside is that there's quite a good deal of expense involved in the move - real estate agent fees alone are enough to cripple the fittest gardener (yes, my metaphor's are starting to get entwined). The point is that physical act of changing house presents you with a new garden - that new garden has been looked after by someone else (probably because they were moving or just in to their gardening). Same with setting up a new learning management system - it's configured and set up the way it should be at the start (hopefully, if you've had it done right) and away you go with a great system.
You may even look after your new garden for a bit after you move - it's always easier to maintain something that's in great condition than to work it up from a bad state. But gradually we have a tendency to sink in to our old ways and the garden starts to look less like the way it did when we started and more like our old garden. For me gardening consists of cutting the grass and (perhaps less frequently) cutting the edges and... that's about the end of my abilities in that space if I'm honest. If you have perfect lawns and not much else that's great, we have roses and fancy bits and pieces and if it's left to me they won't look very fancy in a few months time without help.
The good news is that there are two solutions here. The first is the simplest; get a good gardener in and pay for the solution. If you have the budget to have someone who can help maintain the system the way you want it then that's a pretty good investment. The second involves work unfortunately; you either have to do that work yourself or find someone internally (the wife? the kids? - but only in the gardening sense, try employees for your LMS) who has the capacity AND the interest. If you can't afford the first option and can't be bothered with the second you can either live with your untidy garden or you can make friends with a professional gardener who can at least give you tips and the odd bit of help - same is true with your learning technologies.
Of course just like your garden your LMS has a tendency to grow organically whether you want it to or not. The trick in either case is not to try and stop the growing process (nature will tend to thwart you if you try this) but to shape the process so the end result is something you can be proud of.
Alternatively you can always just move again...