I can't argue with playing it safe, and pulling a full vacuum before servicing an AC system.
BUT, in most cases, even if the AC system leaks down enough the compressor won't even engage, there will still be enough residual pressure in the system to create an overpressure and prevent anything from leaking in. You have to use a little common sense here, obviously if had a line break, had a fast and large leak develop or opened a line completely, air and moisture has leaked into the system. As well, if your system has been totally depleted for years, the natural cycle of air pressure with weather may have got to the point where one day the ambient air pressure exceeded what was left in the system and forced some air and moisture into the system.
But, in most cases, where the system is leaking very slowly and your AC was getting weaker slowly over time and now is at the point where the compressor is cycling excessively or won't engage at all, when it was engaging (cycling) a few weeks before, its very likely there is still enough pressure left in the system to keep any air or moisture from leaking in.
Again, your taking a risk, and you really should never service an AC system yourself unless you have the proper set of gauges (hi and low) and know what they mean.
What it comes down to, with AC if you value the system and don't know what your doing, just take it to a pro to be serviced or repaired, your far more likely to destroy the system and cost yourself far more to repair it doing a ham-fisted diy servicing.
If you don't really value the AC and are NOT willing to pay the money for the Pro, take your chances and do it yourself, not knowing what your doing, and you've got a good chance of destroying the AC. If not the day you add the refrigerant, then a year down the road, when moisture and air in the system form acids and burn up the compressor.