Originally Posted by cdubim
...snip...My best guess is to drill holes through it and install rebar to re-inforce my fence posts and then insert the re-bar into pre-drilled holes in the post...
Um....not so sure I'd go drilling a hole in city maintained property, you may end up with a very large repair bill. It's not wheather what you propose would work or not, it may be perceived that a hole would cause premature degredation of the structure.
Call the city, explain your situation, and find out limitations, and maybe they'll have a suggestion on how to deal with this. Go in, don't call, and have a positive attitude when explaing your situation.