Try giving your insurer a call, I use RACQ, and when I told them I did an engine swap to a 4BD1T, they did not seem very fussed and happily added 'engine replace increase size' to my policy.
There's a bit of a concensus that fitting a turbo to an old model deisel is ok.
As for vicroads, a mod plate was easy too because there were no chassis modifications, the fact you are really only modifying the exhaust I really don't think you will have any problem. I think really a mod plate is only necessary if you have yearly inspections or the possibility of being inspected by transport.
As someone mentioned earlier, 20% sounds like all you need anyway, keeping the boost under 10psi will give you that and not stress the motor too much, if you fit the original garret turbo (or something like it) I think you will achieve your goal.
Wheather or not your gearbox will 'survive' depends more on your driving style IMO. Take it easy on 5th if you have a LT85, otherwise no sweat with the LT95, althought they say the transfer case dosent like too much more power through it, but it will be fine for a while, as I say just drive it like you will be the one to fix it not like you stole it!
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