5 ton AC unit 5+ pounds low on freon - did I get screwed?

Maybe

That sounds about right.

I don't think it would be cooling well at all if it was 5+ pounds low on freon

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New AC guy comes out today, called him on a friend's recommendation. Unit needed some attention, hadn't been serviced in the 2 years I've owned the house and possibly longer.

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You bought a house without having a licensed vendor inspect one of the most expensive repair items involving home ownership?

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R22 at $80/lb.

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That's about right price wise. Now, whether you needed 5 pounds is another story.

R22 is expensive wholesale a jug is over $700. If your unit took 5 lbs, that is not unheard of, but it does seem like a lot to still be cooling. He probably averaged it. You may want to ask about converting it to one of the new gases if he has to come out again. If you didn't have trouble before, it may not leak for a while, there may not be an issue. If there was a recent repair, look at other options.

5 pounds is really low. What was the psi reading at each side?

I would think at 70% of your Freon gone your system would be low enough that it wouldn't cool well and the compressor would run hot.

Seriously you need to look at replacing the old unit with a new one. They are much more efficient these days and that will save on your bill.

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It will be better for you in the long run...

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It will be necessary in the long run since r22's days are numbered.

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New AC guy comes out today, called him on a friend's recommendation. Unit needed some attention, hadn't been serviced in the 2 years I've owned the house and possibly longer. It was still cooling fairly well, not great but not bad considering the condenser is 20 years old. Unit came with 7 pounds loaded from the factory. Is it possible it was that low? He didn't mention a leak. It's R22 at $80/lb.

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The system would not cool the home providing it was 5 lbs short of a 7 lb. charge, it's not possible.
Based on that theory. I would tend to think you have a TXV metering devise, some techs don't know how to charge by sub cooling which is what is required when you have a TXV.
Providing that's the case in a situation like this the tech is feeding/overcharging refrigerant into the unit trying to get his low side pressure up to 68 -72 psi.
Again providing this is what happened, dude will be back because your system won't cool if it's overcharged either.
Start saving your money for a new unit. Good news is a 20 year old system probably doesn't owe you anything.

You have options as well there are other refrigerants available that can be substituted for R22 I use R407C with an oil additive works just like R22 or very close.
BTW providing you have a Piston metering devise you can remove the condensing unit flush the line sets and throw in a r410a condenser and be good to go.
FYI R22 is going for 100 per lb all day here. Plenty more to discuss hope this helps?