You're welcome.
(You can skip to the bottom for answers to your direct questions.)
I've been trying to keep this is as simple as possible and spoke in generalities in order to illustrate the more relevant points. Things that complicate the matter, particularly as regards his individual situation are:
1. How is his ownership structured? Is it held in a regular corporation, a partnership or even a trust? I don't know. If a corporation then there will be little to no direct impact on his own personal tax return. It will pay its own income tax. If held in a partnership entity he owns, the income and expenses will flow directly onto his personal tax return (I'll mention a bit more about this below). If held in a trust for others' benefit the income/deduction may flow to others' tax return and not his.
2. If the income/deductions flow to his own tax return then obviously his other tax attributes affect any benefit/disadvantage. E.g., if the expense of goodwill results in a loss for basketball operations and he has no other income then the expense results in no immediate benefit and is carried forward. If he has a lot of regular income from other sources then that expense from goodwill would be worth 39.6% (plus CA's rate). If instead he has a bunch of LTCG the deduction would be worth 20% (plus CA's rate).
Now to further complicate matters, let's say the items of income/deduction flow to his personal tax return because the ownership is in a partnership or S corp. If so, the question becomes does he 'materially participate' in running the franchise. If he does it's (income/expenses) treated like any other (trade or) business. If he does not, then he cannot deduct the expenses/losses from the franchise. They will be carried forward until he sells it. (Please note I'm simplifying, particularly as regards the latter.)
Now as to your direct questions:
1. Yes, there
may be limits on the tax breaks. E.g., if he doesn't sufficiently work in the franchise he may get none until such time as he sells it ("Passive Activity Loss Limitation'). Otherwise, if the franchise produces losses in excess of his other income he will get no benefit from that excess loss/deduction and it will be carried forward until he has sufficient income to absorb them (NOL carry forward). And again, if the franchise is held in a corporation or a trust for others he gets nothing personally because nothing flows to his own personal tax return.
2 As regards limits on amounts carried forward: If it's a Net Operating Loss from the franchise that's in excess of his other taxable income it can be carried forward indefinitely until used up. If the franchise produces a loss that is limited by the Passive Activity Loss rules he must carry the losses forward until such time as he gets other Passive Activity Income to offset the PAL loss (unlikely IMO) or he sells the franchise and gets to take the deduction.
My apologies if that's confusing. I don't write tax law, I just try to understand it.
Fern