First off, Welcome to the board.
Now that we got that out of the way.
1) fill out your profile, it helps others gauge how to respond.
2) Filling your own cylinders is fine, that is if you know what you are doing.
The cost to do so, is a whole nother story. If you plan to fill your own cylinders,
plan to spend about $4,000.00 to $7,000.00 to get set up. Also figure on the annual cost to maintain the compressor and filters, to the tune of about $100.00 to $200.00 .
3)Filling o2 is again going to cost you. First you would need to learn how to work with o2 , and blending it with compressed air. You would need to get an o2 bottle from a local gas company, pay a monthly rental fee for the cylinder, have all your cylinders o2cleaned, and get o2 filling equipment.
All of the above sounds kinda simple, but there is alot that goes into learning how to work with compressed gas.
I'm not saying that you shouldn't give a fill system a try, what I am saying is that a fill system is a big step that should be taken with care. Learn as much about the system you plan to build before you start, and figure out if the cost of the system is worth it.
I have my own fill station, and am very happy that I built it. Is it less costly than going to the local shop, not by a long shop.. It would be cheaper to buy alot more tanks and have them filled at the shop, and have them ready to go when you are.
Would I do it again, sure I would.
I like to know as much about what I am diving with as I can, and tinkering with my gear is the next best thing to using it to dive.
Good luck, Jim Breslin