3 options, in order of what is most likely to be most cost effective and least time consuming:
https://www.youtube.com/watch?v=r4LZC4larTs
A model specific rebuild kit for a regular floor jack will be $20-$40, https://www.hcrcnow.com/shop/seal-kits, over priced, but worth it because you don't want to be spend time searching for the right pieces individually.
If it's a nice heavy duty jack, that's probably what I'd try first. If you can't fix it, then, whatever, you tried, and learned something along the way.
Now HF as some pretty sweet ones: $190, HD, low pro, high lift similar to mine: https://www.harborfreight.com/3-ton-Long-Reach-Low-Profile-Steel-Heavy-Duty-Floor-Jack-with-Rapid-Pump-Orange-64241.html
I don't know what kind of vehicles your friends and family have, but if you don't need that high of a lift capability or quite as heavy duty:
$130 and would be fine for trucks that are not lifted: https://www.harborfreight.com/3-ton-Steel-Heavy-Duty-Low-Profile-Floor-Jack-with-Rapid-Pump-Orange-64240.html
$80 (coupon this week), wouldn't be great for lower car nor ideal for trucks, but just fine for most coupes and sedans: https://www.harborfreight.com/3-ton-Steel-Heavy-Duty-Floor-Jack-with-Rapid-Pump-64260.html?ccdenc=eyJjb2RlIjoiMjQyNzQ5NTMiLCJza3UiOiI2NDI2MCIsImlzIjoiNzkuOTkiLCJwcm9kdWN0X2lk%0D%0AIjoiMTI5ODAifQ%3D%3D%0D%0A
Consider what kind of vehicle you have, and what kind of vehicle you might be likely to buy next, those sporty side skirts are becoming more common because they are cheap to add on and look nice but will limit your access with standard height jack. Then consider how much you actually do at home, for yourself and/or friends family.
Problem is, most hydraulic repair shops are focusing on heavy duty construction, farm or industrial equipment, because that's where most of the business and the best money is going to be. I really have no clue, but I'd bet labor is probably at least %10-20 more than an average auto mechanic, just like heavy diesel labor is more expensive. Most of them will probably also have a one hour minimum charge, so you are looking at at least $100-$120. If you were going to to take it to a shop, I would see if you can buy the right rebuild kit first, take the kit and the jack in together, because if you buy the parts from them, they will either not have them in stock and have to order them because they don't usually work on small jobs like this, or they will have them in stock, and charge you about %30-50 more than what you can get it for, because that's how that goes. Some shops won't let you bring in your parts because it cuts into their profit margin (or because they have had a customer bring in the wrong parts one too many times and it causes more hassle for everyone), a good shop should allow it though and just charge labor. If you get really really lucky you will find the most honest guy in town who happens to not be busy and he'll say he can do it in a half hour and you'll pay $80-100 for parts & labor. Very, very unlikely.
If it's a real nice heavy duty, high quality jack, fix it yourself. If it's a regular 2-2.5 ton nothing special from the local auto parts store, fix it yourself or buy a new one.
For what it's worth though, if you don't want to do it yourself, I bet you could find a regular old handy man on craigslist or fiver or angie's list who's more than capable of doing it and would do it for $40 labor and it would be totally fine. However, you rely on it to keep you from crushed in extreme pain with serious injury or until you die.
But you never ever trust a floor jack anyway, jack stands go under the car before your body does, always.