You'll need to have a charged system to check for leaks, there's no way around that unless you buy an a/c vacuum machine and see if it will hold vacuum on the system overnight. Having said that, when you turn the a/c on, does your compressor clutch lock up? If it does, you may have enough in the system now to put some dye in and check for leaks.
If you don't have enough freon in there, the clutch will not lock up because of the low pressure switch, and I would NOT bypass the switch to do any testing! You will fry the compressor if you do!
Its obvious that you have a leak somewhere, otherwise you would not need to recharge it. The a/c system is a completely sealed system and normally holds pressure for many years without servicing or recharging. My system was charged back around '07 I believe, when I broke a hose from wheelin'. It still blows cold air today and works like new.
Now, you may have a slow leak, and for that kind of money you're quoting for R12 (plus the license), if it holds pressure for 1 or 2 years, then I'd say not to worry about it and just keep recharging the system with R12. However, if it doesn't hold pressure longer than at least a year, get it charged, put the dye in, check for the leak and repair it. Chances are its the o-rings at the pipes going into the condenser or at the compressor, that's what usually fails first on a/c systems.
Also remember, if your system is opened up, you WILL need to replace the dryer (small little canister next to the condenser.
Remember, you'll need to get the a/c gauge cluster to charge the system also (and Harbor Freight's unit is junk! Don't ask me how I know), and you'll need to check to see if whatever unit you buy works with the R12 canisters.
If your system was working well before it quit on you, you shouldn't worry too much about 134A not getting cold enough. Generally speaking, R12 will be anywhere between 32º and 38º, and R134A in that same vehicle should be between 34º and 42º.
Hard call here, I personally like having R12 in my system, but I've used 134A in other cars with great success, I think the determining factor for me would be whether there's a leak that depletes the system in under a year. If it does, I'd just go ahead and throw 134A in with a little stop leak in it and call it good. If it lasts over a year, then throw the R12 in and be happy.