On my psuedo-MR, I have the following itinerary:
Outbound: SAT-EWR-AVP-EWR-SEA-CLE-EWR-AVP
Inbound, 2 days later: AVP-EWR-SAT

It was booked as: SAT-AVP-SEA-AVP-SAT

I need to transport a few things for AVP that I cannot carry past TSA. When I get to SAT, will they let me check the bag for the 7-segment run, even if there's a layover in AVP before I 'stop' there for 2 days? The first stop in AVP will be the day before the second visit and I don't care if the bag sits there waiting for me.

I have a feeling that it might be easier to just ship the items, even though it'll be expensive... thoughts?

Ive done 3 legs w/o a problem EWR-BOS-MXP-TLV I do believe that 4 is the max allowed, dont remember where I heard that and wont place a bet on it either

Even if it can be done I dont think Id do it unless I for sure didnt want to see the bag or box ever again

I suspect your biggest problem will be going through the same cities more than once - this confuses the computer and makes it spit out luggage tags for a mid-point instead of an end-point. CO Insider commented on this issue here when I flew BWI-EWR-BOS-EWR-CLT:

You'll have to get an agent to hand-tag your bags on the flights to get them all the way through (or to a specific point). These tags only hold a couple of flights apiece, so they will probably have to staple or tape multiple ones together. This creates a ridiculously long "streamer" hanging off the bag, and twice now I've caught a mistake in a flight number on a hand-tag (so double check everything the agent is writing).

All in all, I might ship the stuff. It'll make things easier and more likely to arrive without issue. I'd avoid risks and drawing too much attention to your itinerary - multi-segment trips with a lot of seemingly redundant stops seem to frighten and confuse the counter staff.

I'd honestly have no realistic hope of that bag arriving - mail it to yourself.

Not ever seeing the bag again wasn't a big concern of mine... it's just a few things that my mom wanted that she can't get in PA and don't have much value. I decided to email CO to see if there was an official word (and so I could take the proof to SAT with me in the slim chance they said that it could be done). Unfortunately, it can't (bolding mine):

At least they didn't say "This is a very unusual travel plan and I encourage you to book more sane segments in the future"

thanks now I know its 5 segs and not 4 as I thought

Be careful... they said they contacted the airport (SAT) and they said they can print 5. In theory, they should all be the same, but one never knows.

at most I do a 3er , its just I like to know when I tell someone something its the correct info if asked