If you define a "chip" as feeling ignored and disrespected by the rest of the state, then I would say, Yes we have a chip. It even extends to the fact we bristle when someone refers to Bloomington as southern Indiana. I remember being extremely annoyed when Rex Grossman was referred to as hailing from southern Indiana by national media when he was a UF and with the Bears. I will point out two possible overlooked reasons why I think the chip exists and how it pertains to football.
1. It is probably an overlooked fact, but the lack of direct route to Indianapolis caused a lot of the disconnect. I remember in HS a classmate doing a persuasive speech on why an Indy-Evansville interstate should exist (recently built as I-69). He threw up a slide of a wagon wheel missing a spoke, and then superimposed the state of Indiana over the top. I-70 E-W, I-65 NW to SE, I-74 in between those two, and I-69 from Indy and NE. It really stood out as Evansville was largely ignored. At least 2-3 generations heard that the IndyEvv highway was going to be built without it ever happening. About 10 years ago, going to Indianapolis from Evansville seemed like travelling to a completely other state. It was much easier to get from Evansville to St. Louis, Louisville, or Nashville than it was to our own state capitol. It just added to the disconnect between areas. It's hard to explain exactly how big of a deal the completion of the interstate was to this part of the state.
2. Something I think has impacted SW Indiana football that is often overlooked is that the University of Evansville discontinued its football program in the late 90's. There are currently 3 colleges south of I-70 that play football: Hanover, IU, and Franklin. I think it has been an out of sight/out of mind sort of impact on the SW Indiana region. Marian played for a national championship last week, and St. Francis in the last few years before that. Both really went unnoticed down here. HS football players don't really grow up thinking about playing at the collegiate level. Your upper echelon players will still go play, but that next step down (D2, D3, NAIA level) is not as deep in numbers. And the NFL is almost non-existent. Ben Braunecker (Forest Park) is currently playing for the Bears. Before him - Cutler??? I think was the last NFL player from SW Indiana. And he was a 2001? HS graduate. There haven't been Jaylon Smiths, Tyler Eifert, or Rod Smiths come out of Evansville area lately. My argument would be that there could have been - if the goal of playing college football had been in the forefront.
To answer your original question. Adding a tradition-rich program like Jasper is a big boost to the conference as a whole. VL is another school with successful teams over its history that adds long-term scheduling stability. I don't think they raise the profile of the conference to number 3 conference status any time soon, but it is definitely on the rise.