can be repalced easialy with that ten dollar tool. Your tub floor drain, you simply unscrew it. Remove gasket that seals tub drain at the bottom-you pull it out through the hole. Replace gasket insert new drain. About $25.00 for drain assembly complete with gaskets and over flow assembly.
On that floor drain- as you know when the tub shower is being used-there is considerable weight in the tub. And the weight in the tub puts pressure on the tub floor- so the tub sinks down a little- that weight can be just enough to create an opening -a minute opening that allows water to leak. It leaks there because ,1. the drain is loose-and 2. the gasket is worn or 3. well three is a drain pipe issue under the floor.
In apartment buildings or condo's that sort of leaking happens a lot. I can go in turn on the water in the tub- no leak. Tighten drain-go home. The next time the shower is used-it leaks. I think -darn-should have replaced gasket !
I would think caulking the floor where the flooring material meets the bottom of the tub wall is the suspect leak area based on what you say.
However you did mention flat roof and rain at the time of the leak. On that subject matter- the wind will also come into play. You say it doesn't always leak when it rains. If it's a roof leak- it may depend on the direction the wind is blowing and clogged down spouts so fourth. On those tourch down roofs-leaks form at the seams as a rule.
Get down there and look at caulking at the floor level tub wall-look for minute cracks- push on floor -apply pressure to find probable leak area- and seal it. You remove the old caulk first. Use a razor window scrapper- $1.50 and some paint thinner to remove the silicone caulk.Than run yer bead ,then run yer finger down the bead to bring yer seal into finish effect.
The next time it rains hard-pull that light down and check for leaking.
The roof is a common area and the condo association takes care of that- although everyone pays an equal precentage of the repair cost.
If it's the valve - on the one handle type- there is a replacement part that pulls out. About $20.00 for that. On some of those single handle valves-there is a water cut off screw but not all of them. The directions that come with the replacement part tell you how to remove the old valve insert and insert the new one.
simply remove the handle and the round cover-two screws-and you can than see and get to the valve replacement part. It is not complicated.
On the two handle valves- there are as a rule washers that wear out. Of course the water must be shut off. Replacing washers is not complicated.
Pipe leaks in condo's can be a nightmare to most any contractor because- if a wall or a ceiling has to opened outside your unit or a common area-or a unit below yours than, the pesky condo association must get involved-and if the leak is say-under yer tub in the drain line for example- and the unit below you is where it leaks- thats where who's going to pay for all this !
Whereas in apartment buldings the ownners or the management complny will say do what you must do-we will handle it on the tenant end. Just tell us when you want to do it.
Good luck with that.