Hi, Mike. For what it's worth, I would call in a pro on the roof/flashing. There is a time to let the pro's do it. A real steep roof is one of them. Also, I would check with the condo association. Since they are responsible for the painting, they should be responsible for the caulking that goes with the job.
Regarding the bathroom floor, mine is actually crowned so any water runs toward the walls and out of the center of the floor. You do not notice it unless you are looking for it, but it's there. I understand that most bathrooms are built this way. If you have cracking of the floor, you would want to have it checked out. If you see water under the tub (in the basement or whereever) soon after you have had a shower, you would want to check it out. If you don't have either of these, it is probably the way it is built.