try... query

I'm attempting to get my head around preventing resource leaks, using try and return. In fact I thought I had understood the mechanisms well enough to use them and had come up with a structure like this:
proc allocateResources {} {
     set obj1 [Some_mechanism]
     try {
         set obj2 [Some_other_mechanism]
         try {
             do_various_other_stuff
         } on error {message errorDict} {
             $obj2 destroy
             return                                          \
                 -code error                                 \
                 -errorcode [dict get $errorDict -errorcode] \
                 -errorinfo [dict get $errorDict -errorinfo] \
                 $message
         }
     } on error {
         $obj1 destroy
         return                                              \
             -code error                                     \
             -errorcode [dict get $errorDict -errorcode]     \
             -errorinfo [dict get $errorDict -errorinfo]     \
             $message
     }
     return [list $obj1 $obj2]
}
If all is well, I expect the caller of allocateResources to destroy the objects when it has finished with them.
There are a couple of areas of this code that I don't completely (?!) understand:
1) I was assuming that if there was an error in do_various_other_stuff if would be caught by the inner 'on error' clause, which would delete obj2 and raise another error that would be caught by the outer 'on error' clause, which would delete obj1. Experiment suggests that this doesn't happen and the outer 'on error' clause isn't executed.
2) Originally, I wasn't including -errorinfo in the return statements in the 'on error' clauses, but I found that the stack trace didn't properly identify the line causing the error. Including -errorinfo seems to have cured that problem.
So,
Q1) Have I misunderstood the way try... works, or is my problem elsewhere? I realise that I could do away with the nested try... statement and check whether obj1 and obj2 exist and only destroy them if they do, but that seems clunky.
Q2) Have I coded the return statements properly to get the error information to propagate correctly? I have a vague memory of doing it this way sometime in the past only for some other issue to emerge that I corrected by not using -errorinfo.
Thanks,
Alan
PS For what it's worth, I am using a home-built tcl9.0.0 on Linux Mint.