Not really familiar with St. Charles football but why do they seem to struggle so much? What are some of the issues if a well respected coach like Jacoby couldn't get it going?
It's the sum of five things: 1) tradition/lack thereof, 2) marketing as a program, 3) marketing as a school, 4) lack of territorial pull, 5) single-sex vs coeducational
Tradition/Lack Thereof
Of the five Franklin County schools in the Diocese of Columbus, St. Charles has the least football tradition. As mentioned, it only has one CCL championship in ~50 years (2013.) It has zero playoff wins. Because the CCL schedule has always been two games (under the Gold/Silver alignment) or three games (current alignment), and the fact St. Charles is super-susceptible to waxing-and-waning periods (more on this later) they also never have an identity on their regular season. They play teams of varying sizes/competitiveness from all over the state (typically they lose to them) and in the local area they either get throttled by the OCC (see: games vs UA and Pick North) or pull off stunners now-and-then. Two years ago, they beat Scioto in week 1 and followed that up in October by only scoring eight (8) points in a losing effort versus a
Division 7(!) public school.
They also have ran into issues with this last decade of kids getting ejected for fighting (weird for SC), and in one case they tried to play an ejected kid the week he should've been suspended.
Marketing as a Program
This goes hand-in-hand with the below two points and the point above. St. Charles has had some turnover (3 coaches in the last decade, including the ill-fated Jacoby regime.) DeSales and Hartley have had the same coaches for a decade plus. Wiggins (SFD) and Burchfield (BH) are known in the schools they rely on cultivating rapport, and later enrollment, out of. Again, SC the majority of time is mediocre at best. What passes for a "good" year at SC is a mediocre year at SFD and BH. Even with Watterson having an unusually rocky last decade, their prestige and tradition trumps that of St. Charles.
SFD, BH, and BW all have the bedrock of multiple, vibrant CYO organizations that correspond to their territories (which SC has neither of, CYO bedrock nor territorial advantage.) DeSales has the St. Anthony + St. Matthias + St. James the Less combined program that encapsulates the Linden area, they have the 45-50% attraction of kids out of St. Matthew in Gahanna as well as the similar (if not better) rate of attraction with St. Paul in Westerville. Hartley has the east side program of St. Catherine in Eastmoor + Christ the King in Berwick + Holy Spirit in Whitehall + St. Mary in German Village + St. Pius X of Reynoldsburg. Plus the plurality (or some years, majority) of kids that don't go to DeSales out of St. Matthew in Gahanna. Watterson has the Northwest Saints program (Agatha, Andrew, I believe Trinity/Our Lady of Victory in Grandview/Northwest Blvd adjacencies is also this), the Immaculate Conception-Our Lady of Peace combined program that services Catholics in Old North and Clintonville, and St. Michael in Worthington. I believe St. Brendan of Hillard and St. Brigid of Kildare (Dublin), where Urban Meyer's son went, also are feeders into BW.
St. Charles, meanwhile, has none of these. They just get a sprinkling of 25-30 football kids across the entire CYO: some are good, some are not great. It's a mis-mash. And you never really know who all you're getting, either.
Marketing as a School
St. Charles' academics are fantastic. Indisputably fantastic. Their curriculum is also
very rigorous, and this is well-known. BH, BW and SFD also have tough academic schedules -- don't get it twisted -- but SC's is hardest. It is a widely-spoken belief (if not fact) that your first semester/freshman year at St. Charles determines whether or not you're going to make it there. For many parents, many parents, this seeps into their minds and the idea of trying to juggle football as new high school students at a school that will invariably kick your butts with homework and testing scares many kids *and their parents* away.
We are also in an age (21st century) and geography (Central Ohio) where a school such as St. Charles has to compete with high-end suburban districts (Dublin, Olentangy, Bexley, New Albany et al) for the well-heeled "super-academic" types as well as nonsectarian high-brow*high-standard college prep schools (e.g. Columbus Academy, Wellington). On the Catholic faith and private school atmosphere merits, alone, it competes directly with DeSales, Hartley, Watterson, Ready and to a certain extent even the outlying Catholic schools in Newark and Lancaster. If the personal value and opinion toward athletic excellence is on the same bar as academic excellence, SC is losing out 95-99% of the time on incoming Catholic freshmen to those schools. If being a part of a solid football and wrestling program means as much to a kid as does their schooling, they're going to DeSales or Hartley. Not SC.
Territorial Pull
See the above. The only geography in Columbus/Columbus metro that St. Charles has any direct leaning on has been the East Side of Columbus, which has been withered away by the resurgence of Bishop Hartley these last 15-20 years. In every aspect. Football, academics, faith. Getting kids that live in northern Franklin/southern Delaware Counties is great for SC -- it's not reliable, though. Not nearly the way it used to be, or could be, with St. Charles being a bully on the block for any geography east of I-71.
Single Sex vs. Coeducational
It's an all-boys school. Hard sell these days. Especially to middle-class families who have boys and girls within a couple years of the other. The co-eds win out most of the time on those families.