First off - welcome to the forum!
To me, these problems seem to be taking care of themselves.
For problem 1 - if the dooger is no longer tearing, the problem might well be over. These things can happen when irritants get in the eye.
For problem 2 - unless I've misunderstood something, seems the dog has a raw tail that is healing slowly. What originally caused this might have been the airborne construction materials that irritated the tail and he started chewing on it. I'm guessing here of course. But if that is the case, I would expect it to heal up on its own within the next few weeks.
Obviously a vet visit is the safest route any time you are concerned - but I would not expect this to cost hundreds of dollars.
I'd be very curious to hear what other members suggest.
any chance you can post an image of the raw tail?