Which compressor?

That really depends on your budget, there are big differences between compressors. For the cheaper ones, you are kind of rolling the dice. Some guys have good experience and some have bad. The bigger your budget, the better off you will be, in general.

Filling bottles is a whole different thing then filling just guns. Small portable compressors aren’t meant to do that generally.
 
The best compressor you can buy for $1000 or less would be...

The Yong Heng for under $350

The"simple version" least expensive does not have a water separator you need one.

The "auto stop" version shuts off near 3000psi. Probly not what you want.

So you likely want the "Hardcover" or 'Set pressure' versions your choice on the 110V or 220V.

https://www.aliexpress.com/item/32824234795.html?spm=a2g0o.store_home.productList_13760454.subject_2

Keep them cool, the oil topped off to the red circle in the sight glass, and don't fill past their spec which I think is 4350psi, a little less is better than the max, and the Yong Heng should last for years unless you get a bad one. I did my first oil change at about an hour far longer, between changes, after that.

I have two YH compressors. Bought the second as a backup for the first as I fergot to turn on the coolant pump several times and overheated it until it smoked. It did not like it but it still runs fine. Still I did not trust it after that. I added a switched outlet, to the system, so it turns the pump on before the compressor will power up to keep me from doing that from now on. The second one, my back up unit, died in about two months bad QC from the factory. Cost me a $12, for a new second stage piston, and an hour to repair it. Then to add insult to injury I fergot to put the oil in, the latest unit, after I put it back together and ran it for a couple of minutes without any oil. Somehow it still runs fine. The #1 unit that I was worried about, cuz I overheated it so many times, just kept on filling my guns and tanks till I got #2 repaired and retired it.

I do not fill past 4200psi as when I do, all too often, I blow a burst disc. This does not happen on the first or second fill but soon thereafter.

The temperature sensor only measures head temperature so running it much over 20-30 minutes can overheat the motor and other parts even if ice is used in the coolant. Ice or a container of it, in the coolant, is a good idea especially if you are like me and do not use the full five gallons of water as suggested in the manual.

Keep your water supply level with the compressor to be kind to the pump and assure a good supply of coolant goes through the compressor.

Keep your moisture filters, guns and tanks being filled above the compressor to help keep the moisture out.

Purge the system of moisture for a couple of seconds every five minutes while in use.

Change out your small YH filter every twenty minutes and set the old one out to dry and use later.

Add a better filter if needed to be sure more moisture and any oil smell is removed from the system. Many of us use this Tuxing three media filter although, if you feel the need, you can change media types at any time.

https://www.aliexpress.com/item/32891898253.html

A smaller one will probly do for many.

https://www.aliexpress.com/item/4000960926898.html?spm=a2g0s.9042311.0.0.2a034c4dL0nrJU.

Bleed the pressure before you turn the unit off and let it run a few seconds to get the better part of the moisture out of the system. I have found that I blow less burst discs if I bleed before shutting down so I do this religiously.

Let the coolant pump run for a few minutes after shutdown to cool things off.


 
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I have had the AV-4500 psi compressor for a little over three years now filling two tanks (60 and 30 minute tanks) and haven't had any issues with it. It's not very portable, but I use the tanks that are. I like that it is self cooling and runs quite for what it is, and that it has a built in large filter that is standing vertical that the water has to get up through, which it never has. I also like that it cools the hot compressed air a bunch before it goes into the tanks with its coiled lines so I can keep what I put into the tanks without loosing any psi hours later like warm tanks do when they cool back down.
 
I have a Yong Hen with the settable pressure cut off. Runs flawless but I only fill my guns (2 180cc Hatsan cylinders, a 100cc wildfire and 2 50cc pistol cylinders). Longest time to fill is 45 seconds. I also have a DAVV (or Davy as it is listed in the literature under both names). This is a simple version with no set pressure. I keep it at my Dads as he has a PCP and I go over there to shoot once in a while so I don't have to lug a compressor back and forth. This has also preformed flawlessly. I have about an hour on both compressors and have changed the oil on both 2 times. No issues.