My uncle works for a county and I knew he would be involved in these types of things so I asked him how it usually works. Road maintenance should be the county's responsibility since there is no provincial park etc. Little roads/accesses like this are extremely low priority for these counties so they usually get forgot about/ignored.
What he recommended is to talk to the county and ask them if they can fix the road up a bit. If they say not in the budget then offer to fund it(via the sources you were thinking of) and they should agree to it then. Doesn't sound like any further permissions etc would be required since they are the ones that are supposed to take care of it anyways.
Modifying the boat launch gets a lot more involved and would require permits
and permission etc. Having been there this year I don't think it is necessary though. That little lake doesn't need a launch capable of big trailered boats and it already has a better launch then many other of our lakes so I would leave it as is.
If you haven't already talked to the county that is where I would start. You might be able to avoid a lot of these headaches although might have to settle for a bit less then you were originally hoping for.
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