Haven't thought about the bootblock, good one.
Track2File might be useful yes.
Whats the difference with that HRTmon and the one built into WinUAE?
There is even a Add36k - http://aminet.net/package/util/misc/add36k
Not sure how this affects memory and bitplanes tho.
I looked into some of this, but i was a bit low on diskspace (especially with all apps decrunched). Reloc-crunchers seems to put certain decrunchers at fixed-points in memory (which might be put into chipram).
In the meanwhile i created a small disk for graphics ripping, 3rd-day seems to be pretty cool. tho it doesn't like the KS2/AGA combination much.