I did a bunch of searching, and was able to find info about splitting a direct flight, but nothing about this.

My question is, can I book two segments and then call and have them pair them so that an actual connection is listed (which would help in the event of IRROPS, correct?)

The flight is AAA-BBB and the times that are most convenient for me are ~$40 cheaper (via IAH connection-which is the cheapest) when searched via the multi-city search versus just a roundtrip. The IAH connection also comes up when I do a regular roundtrip search but it is ~$40 higher. So the connection is allowable in IAH it looks like but I just want to get it to price out in my favor.

Not sure if any fare rules are being broken or if this is legit/possible?

Thanks in advance!