Well i've only use an A500 and A1200..
Currently have the A1200 here..
OS4 will not work on a classic Amiga, you need an AmigaOne for that. OS3.9 with BoingBag 2 installed is the latest you can go.
You'll want at the very least 16meg of ram, 32 preferred.
3.1 roms are needed for OS3.9
As for hooking up a PC monitor.. Yes, do that, with the Multiscan Productivity screenmode in the Storage/Monitors/ folder, you will need to use a TV or old monitor while setting that up though.
You can make the converter yourself, there are diagrams on de.aminet.net/ if you know where to search (can't think of anything specific at the moment)
[Edit, look at these URL's
ftp://de.aminet.net/pub/aminet/hard/hack/ami2vga.lhaftp://de.aminet.net/pub/aminet/hard/hack/VGA_Hack.lhaYou'll need WinRAR to extract the .lha's and an ILBM picture viewer for the pics.
]
You can email me at mick_jt@hotmail.com