'Conversion' is not a lot of work. Hell, you don't even need the fittings with a proper set of manifold gauges; with many, you simply unthread the r134 couplers off the end, and are left with the r12 ones. I'd recommend the fittings, though, since they're cheap.
Oil is circulated throughout the system. Yes, the compressor 'holds' oil, but it's generally in the same sense that other replaceable parts do. E.g. you'll add roughly as much oil for a condenser replacement as you will a compressor replacement in most cases. It is nigh-impossible to remove all the old oil, even with a long evac (suction held on the system). But you should try to get out as much as possible, as mineral oil will not circulate properly with r134.
You will add ester oil to the system (not PAG). Make sure the r134 you buy doesn't have oil in it. If it has dye in it, there is oil.
Drier is the only hard part that really should be replaced. Ignore people who tell you your old hoses are going to explode or some such garbage. R134 is more leak-prone, but there is no danger other than some lost refrigerant. I would just add some dye (put the concentrated stuff in with the ester oil) and charge it up, and see what happens. You'll know where any leaks are- will probably just be from old o-rings.
I would highly recommend buying or borrowing a real set of gauges, and not charging based on weight. Old compressors don't always cope with the 'proper' amount of refrigerant, and the system may perform better with slightly less. I charge based upon low side pressure- when the compressor is on the verge of being unable to pull the low side down to 30-35 pounds or so, you're done.
You've also got the conversion factor...even by weight, you would not charge to factory spec with r134. There's a percentage that most people use, but I don't remember it off the top of my head. Again, go by pressures and general system performance and you won't need to worry about it.