Ok let me get this straight. You want a dock on pilings because you can't have permanent. Pilings kinda makes it permanent. You also need to be able to drag it up a hill and a lift? Sounds like concessions are gonna need to be made. What Chris described with maybe an air dock in the middle sounds like it would be closest to fitting the criteria still a pain in the ass to move.

This dock thing sounds to difficult, let us know when you get the stripper pole.

I should've been more clear wooden post and not piling. With the boatlift there's a marina that picks up and drops off your boat lift with there boat. The path with the steps are definetly wide enough for 4' wide sections. In fact when our current dock gets taken out we have 5 4x8 sections all stacked up next to each other on the path. We have the professionals move the dock into and out of the water when we need it to be.

So what's wrong with how you currently have it set up? And, for the record, pictures would probably tell a better story... Also...perhaps some mention of how much you are willing/able to spend? Depth of the water? Plans for actually stabilizing the stripper pole?

The problem with the current set up is that you can only have one boat at the dock. It only goes out 24' with a parallel spot of 12' to dock my boat at which I was just able to do.. I would like to have there at least be able to have two boats at the dock. Also the dock is starting to fall apart. All the more reason to have a new dock. From 16' to 40' from the shore it goes from 3' to 6' deep. 24' from shore is 5' deep. No plans for the stripper pole sorry about that. I have awesome neighbors up there and would like to keep it that way. I would like to have a bench on the dock. So yes to add to it the dock is too small. I don't know how to work windows 8 to upload the photos sorry.

BINGO, my buddy brougth his lotus over my house and we filmed 4 hot chicks (skanks) stripping and frolicking as they washed it, by the time we finished there was a crowd of all my neighborhood bros and their pissed off looking wives gathered on the other side on my canal... i got mad props from my bros over that one, but the at least wives new better than to call jonny law and ruin the show. lol

Thinking outside the box, you say you are on a hill, could you drive a crane to a location where it could lift a decent sized dock complete into the water?

No I'm looking to have 4x 8 sections for the dock. Most likely the installers will be carrying the sections down the path which do have steps. and a railing. So yes the path is wide enough for the sections. The driveway is about 30' from the path. So it's a straight shot for them.

Lots of Ideas Here Nick
 

Click around this website for some ideas.

https://www.summersetmarine.com/

What lake are you on?

I have had a Hewitt roll a dock for the past 7 years that works great.2 32' docks hinged together that I hook my truck to and pull out every year. Also a 10' section hinged to our sea wall that attaches to the dock as well. Many configurations available, love the easy in and out compared to building the dock every year.