Sorry if this has been posted before but I couldn't find my exact question after 30 minutes of searching. About me for some perspective of my questions. I do not shy away from DIY work, though plumbing is not my strong point. Just something about potential and usually immediate water damage that worries me.

My issue is that I have an acrylic shower base in a custom tiled shower on the 2nd floor that was installed about 4-5 years ago. The other day I noticed water on the ceiling of my 1st floor just under the shower. As I inspected the drain I came across my first Oatey No-Calk drain (PVS model with stainless strainer. I really didn't know what I was looking at until I found your forums and have learned quite a bit. The compression nut was very loose and came off with my fingers. I am certain that is what was causing the leak, so on to fixing or replacing the drain.

Given the relative "young" age of my shower I'm tempted to simply get a new gasket for the drain pipe and compress it down as instructed. However when I was about to remove the old gasket I noticed the drain pipe has what I consider a LOT of play. As in I could grab the pipe using just the pressure of my fingers on the inner walls of the pipe, it moves up and down extremely easily. We are talking easily 2" of play (1" up, 1" down). This concerned me to the point that I imagined the pipe falling into the floor if the old gasket were removed forcing me to cut into the downstairs ceiling.

So the questions really are this:
1- Should the drain pipe have this type of "play"? My gut tells me no but hey, I have never installed a shower before.
2- How far above the compression fitting should the pipe sit? I don't want to stress the pipe pulling it up or leave it too low.
3- Should I go the route of replacing the gasket only or maybe remove the entire drain in lieu of one of the wingtite units (very impressed with their product given online videos and reviews).

Some key points I've seen asked in other posts so I'll pre-empt what I can:
-I currently have NO access from below the shower. In order to do that I'd need to cut away drywall and I really hate installing drywall. Fun as anything to smash through and demo but I am not a spakle and tape person especially on a ceiling.
-The shower bottom (acrylic) does not flex, least not that I can see, feel, or hear. I wasn't present for the shower install but I did the demo of the old shower/tub combo so I know what is under the shower. Our floors are standard 3/4" plywood.
-I am recaulking around the entire shower base where it meets the ceramic tile. This is being done both as cleanup (mildew, etc) and to make sure none of those seams were the cause of the leak.

Any help you can provide would be most appreciated. My wife loves our shower and the more days she's without it the more days I'm in the dog house.