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One of my first customers had a major drain issue necessitating the whole area be dug up to replace. These pictures don’t really show what’s going on but it’s better than nothing. There’s very well established roots from mature trees that are upturned and sticking out here and there. Is this possibly something that a guy with my resources could tackle?

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Let’s see how my actions might precede if I didn’t have you chaps to keep me from doing anything stupid or way above my pay grade.

First of course I’d blow out the leaves to see exactly what’s going on.
I would think to go in with a chainsaw, loppers and maybe a sawzall and remove the exposed roots and halfway upturned shrubs. After that perhaps rent a burly cultivator and break up the mounds and areas without roots to rake and redistribute the soil, maybe add quality fill dirt. I’m planning on renting a slice seeder for my terrible backyard when it starts raining regularly and something like seems like a dandy way to pay for it.

I don’t need this job and it would be getting past my cutoff for taking major jobs in the Carolina heat but I’d be willing to consider it for the experience. I don’t think heavy machinery is “necessary” but the important phrase is “I don’t think” lol. She’s a super nice old lady I could easily break it up into 4 hour shifts on Saturdays. This is a much a question if I could/should even consider this as what would a major landscaping contractor use and do? I wouldn’t even try to rent heavy equipment so no need to warn me about being stupid and getting hurt or sued.
Definitely clean up what appear to be magnolia leaves. The area in question looks to be shady enough as it is. You will want to loosen whatever soil you can once the area is cleaned up of leaves and debris, add healthy enhanced top soil (soil/compost blend), level the area with a soil leveling rake, and then either seed or install sod. If the area is as shady as it appears, you may want to go with a shade tolerant seed blend that contains a fast germinating seed. Once the area has been generously seeded, and the seed has been gently raked in, cover with either peat moss or clean straw. Depending on your geographic location, it may behoove you to tackle this at the beginning of fall, unless you choose to use sod.
P.S Be careful cutting roots. If any shrubs that have been uprooted are salvageable you may want to try to reposition the shrub and replant those roots with some amended soil and then give it a long but slow watering so that the shrub has a chance to reestablish itself.
I hope this info helps you out.
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