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I've also been spending some quality time outside with the overgrown landscape. I honestly don't think anything has been pruned out there for at least 10 years. I cut down a couple of scrawny trees which went to seed next to the foundation. They weren't big enough to cause any damage, but they were about to touch the gutters, so I know they've been there a while. The evergreen bushes were about twice the size that they should have been allowed to grow, so I cut out a lot of the lower growth to expose the roots. They look much better now, in my opinion. By the patio, I had an evergreen which was so heavily overgrown that the best thing for it was just to remove the whole thing.
Our plan for the landscaping has changed a bit now. We're going to wait until next Spring to do any real major work outside so we can do all the landscaping in one shot (when we have money). The interior renovations are going to take every penny we have right now, and I've got enough on my plate without worrying about the landscape too much.