The comparision with Dunfermline, Falkirk, Morton and Airdrie are interesting.
Dunfermline has larger attendances on average than we do but is still recovering from chasing rainbows under Masterton. Which is similar to were we were after the "save the jags" season. I suspect Dunfermline will be back challenging for a spot in the SPL in about 2 or 3 seasons. Dunfermline have made 3 cup finals and played in Europe in the last 20 years so arguably the did better than us.
Falkirk have comparible crowds to us and have similar ups and downs with owners. Right now they are underperforming and desperate for a new owner and chairman to take over. They would still probably be in the Championship if they hadn't experimented with importing non-league english players last season under Hartley. However Falkirk have made the Scottish Cup Final and qualified for Europe in the last 10 years. So their highs are aguably better than ours.
Morton and Airdrie (current incarnation) are clubs that have less support and less financial backing than us. They are on a par with Hamilton and Livingston. However Morton have never dealt with Cappielow properly to develop the income streams that Hamilton rely on and the Hugh Scott era almost ended them so getting a benefactor like Douglas Rae wasn't enough to repair the damage caused so far.
Airdrie overspent in the 90's to get to top league then went bust with a stadium thats now a white elephant and have never recovered. They could adopt a model similar to Hamilton and Livingston but it will take a long time for that to bear fruit and with crowds down its hard to see how they will be much more than a team that yoyo's between League 1 and the championship. Arguably Airdrie are more comparable to Clyde than they are to us.
Personally I think there is a group of clubs outside of Rangers, Celtic, Aberdeen, Hibs, Hearts and Dundee United that we are in. That group contains Motherwell, Kilmarnock, St Johnstone, Dundee, St Mirren, Falkirk and Dunfermline. So if we are well run for a 15/20 year period we should be consitently in the top league and have the ocaissonal cup final appearance. However we have not appeared in a cup final or major European competition in nearly 50 years. All the others in the group I described have achieved that in the last 20 years or less.
ICT and Ross County may in time be clubs that sit within our group but I suspect they are being financially supported beyond their true means and over the next 20 years may settle into being solid Championship clubs rather than yoyo clubs. However both of them have again appeared in a major cup final in the last 20 years and ICT have appeared in europe.