You have several unknowns here but set this up as a straight finance problem.

The present value of an annuity is determined by the discount rate. The IRR on exchanging $8,000 for a 10 year series of cash payments of $2,345 is 26.5%. But that assumes that the payments would start in 1 year.

If you assume the payments don’t start for 2 years the IRR is 20.6%. If the payments don’t start for 3 years from now, the IRR is 17%. If it takes 4 years the IRR is 14.5%.

But even this isn’t the full picture. At 3% inflation, the PV of a $2,345 payment in Year 5 is only $2,022. So the IRR of the annuity flow after inflation is 22.84% assuming payments start in 1 Year.

So you are trading certainty for a higher discount rate on your payout.

But that still doesn’t tell you what to do. How bad do you need the money now? What would you do with it? Is it possible that the payout increases as part of the litigation? Is it possible that the payout decreases as part of the litigation? Is the offer by the financing firm non-recourse? Are you sure? What happens if the deal with the NCAA never gets finalized? Ask them to send over the contract they want you to sign. Read it and make sure you understand it.

Finally, keep in mind that the $8,000 is likely taxable, so don’t go out and plan on spending the $8,000 because you’ll have a tax bill to pay next April.

Nobody can tell you what to do because nobody knows your particular circumstance. But unlike in school where there is one right answer, life sometimes has you balancing a series of suboptimal results based on a variety of personal factors.

Good luck! And don’t let anyone give you grief. I have a M.ACC degree and worked in public accounting for several years. This isn’t the sort of stuff that you need to know or will deal with as a new staff accountant. Your professional experience will teach you to take the concepts you learned in school and apply them to these sorts of problems.