I don't know if this is the plan for certain, but the repeater penalties only become a concern if you continue to raise payroll and live well above the tax line. Take two hypotheticals of a 3 year sample:
A: under LT, 10 million over, 18 million over; 7.4 million in total penalties
B: 5 million over, 10 million over, 15 million over; 13 million in total penalties
In neither outcome are there draft penalties, and you're saving less than 6 million in penalties across a 3 year span by ducking under this first year. Plus in the Cubs case, after year 3 (2026) they have an easy opportunity to reset(Bellinger, Happ, Seiya, Taillon, and Hoerner all FA), so there's less of a slippery slope. Not to mention a new CBA starts in 2027.