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Driveway on top of retaining wall maintenance Hello! We…

Driveway on top of retaining wall maintenance

Hello! We bought our first home almost 4 years ago in the New England area and while we were prepared for most of the maintenance items that have come up something that we didn't even consider is that our "driveway", which we own but runs parallel to the road, is also on top of a retaining wall. Recently we had a couple \~3" deep pot holes and one true sinkhole appear on the driveway with the sinkhole having a clear hole leading to and through the retaining wall. We've fixed and patched them as they appear but that's made us think about the overall condition of the structure and I have a couple questions.



First, there is a gap between the driveway and the retaining wall. Should we keep this gap for drainage or seal it to prevent water intrusion? Most of the retaining wall's face is sealed and there's a small section of the gap that was previously sealed so I was planning on sealing the rest with concrete or waterproofing mortar, but it's a lot easier to double check than rip out the mortar.



Second, who should I contact to check if the presence of the potholes is because the underlying substrate is losing integrity or just that there is water intrusion and we need to seal wherever it's getting through? I'm at a bit of a loss on who to contact, it seems that driveway companies wouldn't know about the retaining wall and retaining wall companies aren't used to having the load of two+ vehicles within a couple feet of the wall.



Here's a few images of the wall/driveway: https://imgur.com/a/diNNGOu
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