PCP (pre charged pneumatic) airguns require filling to pressures much greater than a shop compressor. The air tubes on the rifles are rated between 3000 and 4000 psi. A shop compressor generally runs between 90 and 125 psi. Most shooters wind up with either a SCUBA tank (which are generally rated to 3000 psi) or an SCBA bottle that holds 4500 psi. There are paintball and dive shops that can fill these tanks, but you do need to check on whether they can fill to the higher pressure before investing in an SCBA bottle. Those of us (like me) who do not have a place close by that can fill to 4500 psi, tune our guns to work at a bit lower pressure (2000 to 2500 psi) and fill with the SCUBA tanks.
Filling with one of the bicycle style hand compressors, is not too bad if you have a bit smaller air tube on your gun. Trying to fill one of the bottle guns would be only for one who likes punishment.
Also, you are kind of missing the point with airguns. Airgun pellets have a much poorer ballistic coefficient than any bullet. What this allows, then, is long range practice for wind estimation, hold over (click adjustments) for various ranges, etc. but at distances much shorter than what is needed for highpower rifles, or even .22 rimfire. For example, a 20 ft-lb .177 airgun has about the same wind drift (in terms of angle for a given wind speed) as a .223 does shooting 77 or 80 grain match bullet at 600 yards.
As far as precision goes, modern airguns are getting to the point where less than one minute of angle at reasonable ranges is quite common. The better guns and shooters (who are willing to do some tuning) are turning out shooting 1/4 MOA at 25 meters in benchrest matches. These matches are outdoors where wind plays a significant part. Yet, these shooters are judging the wind well enough to punch out the center of the benchrest target time and time again.
Now, getting started with a rifle that is accurate enough, and is fairly easy to fill with a hand pump (or filled with a SCUBA tank), and within your budget for the whole kit, I suggest that you look at the Brocock Compatto, and the FX Streamline (or wait for the Dreamline which is more tunable).
These rifles are very good, but are at or slightly below the $1000 mark. A Hill pump will run you about $200, while a SCUBA tank with fill device will set you back about $375. A large SCBA bottle will cost about $600 and has only a 15 year lifespan, but you will be able to fill your rifle all the way many times before you need to get it refilled. You will also need a scope, but that is something you will need to decide for yourself.