Shower Drain Leak

So, we've had this leak fixed once before by a handyman whose work appears to have been pretty shoddy. Water started coming through our ceiling again last week so I cut open the ceiling to try to identify the source. The pictures below show where I think the water is coming from and what my drain looks like from above (it looks a little rough as I took a quick first stab at trying to remove it).

Any suggestions on the easiest way to repair this? I've read about the Wingtite and am wondering if this would work or if it can be done cheaper simply by replacing with better-installed drain parts.

Thanks for any and all help....Chris

If you can wiggle the drain, it needs to be thrown out.
I install new drains using Silicone Sealant.

Putty tends to dry out over time and get loose.

So you think that based on the location of the leak, I should be able to fix it by just replacing the drain from above and using silicone with the new drain?

Thanks.

Your existing drain is glued to the pipe.
You will have to cut the pipe, couple it and install a new drain.
It will be easier to do it from below.

Unless you can loosen the nut, push the drain up and squeeze some silicone under the flange.
No, forget that. There is no good way to clean the surfaces.
Remove the dang drain, and clean up the shower pan, then put down the new clean drain with new silicone.