Good question, but tough to answer without asking a few questions myself

You own 3 (higher end) pcps iirc...clean dry air is important and hand pumping is not an option with your health i imagine.
Questions to consider:
-How often are you shooting your pcps, and what caliber/tank size are they?
How long are your bench sessions?
When one is empty do you grab another or prefer to fill it and keep shooting just the one?
Do you only shoot at your place, or do you go elsewhere sometimes (taking a small tank is much easier than the compressor and filter)
I have the Hill Evo as well with a decent filter setup and direct-fill my 2 pcps.
Only once did I ever refill a pcp (was midway tuning my Ghost) and go right back outside and keep shooting it.
Now if I get that RAW .357, or something unregulated, or just bigger caliber than .22 I'd recommend a small tank to go along with your outfit.
Doing so will likely murder your small compressor in short order, and you will need a bigger/better one....and so it goes.
I'd run what you have till it dies, then upgrade to a better compressor and maybe a 2 or 3 liter bottle.