...Rogers has not become a successful conglomerate by penny pinching....
You believe that? Okay....
Spending a lot of money, and spending a lot of money WISELY are two different things.
The Jays' ability to compete is hampered by economics, (most of their revenue is in Canadian dollars, and most of their expenses in American), they have the disadvantage of playing on artificial turf, and they're not based in the USA.
Most free agents are age 30, +/- a couple of years. Playing on turf shortens careers. Older players consider that they might be costing themselves one last fat contract at the end of the road, if they sign here. Can you name a top tier free agent who has signed with Toronto for more than one year since Roger Clemens? I can't. It isn't enough for the Blue Jays to offer the same amount to free agents, they NEED to overpay. That's how they ended up with a second division roster, despite a high payroll: they're paying top dollar for second tier talent.
While Toronto is, statistically, a safer city than pretty much every American city, it's still a backwater town, as far as TV is concerned. They get less exposure on US TV, which means less fame, and the endorsement money which comes with being a household name. Tony Fernandez couldn't understand why he was paid so much less than Ozzie Smith, despite being similar in statistical performance. It had a lot to do with Ozzie being well known, even to people who don't follow baseball, and Tony's facial acne and religious fervour didn't help either, "Me, I turn double play for Jesus".
Vlad Guerrero isn't getting much endorsement money, because he can't, or won't, speak in English. Do you remember the TV ad with Lloyd Moseby and George Bell? George: "Gway pwomo, Loy, telus somo".