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I'd probably pick consultant, because it's the knowledge being tapped, rather than a patient being seen. YMMV, I could make a case the other way as well. However, since both are SE income, in the long run it doesn't matter. FWIW, I have had plenty of psychologist/therapist tax clients whose 1099s from insurance companies have, in the same year, run the gamut between medical, consulting, and "other" income. We put it all on their Sch C, since that's where it all belongs. Never a question.

This is an unusual situation. Usually an implied life estate is used to establish a stepped up basis when the house is sold after the death of the transferor. But in this case the transferee died first and the house reverted to mom. So as I see it, there is a question as to whether the life estate terminated between the time mom went into nursing care in 2020 and death of daughter in April of 2021? Otherwise there is no step up in basis.

He could get the same amount of the inheritance without taxes and SE tax if he takes it as inheritance instead of payment for work

From the original post, the son paid for materials & supplies with that $20k. That is a completely valid claim against the property & there should be no issue with him being reimbursed at close. If for materials, he could put a lien on the property. I had a case (that I got after the house sale dust settled) of a surviving spouse who was not part owner of the house - it was 100% owned by the spouse who died - who paid all the house costs until the legal paperwork was settled to the point of the house being salable. Mortgage, maintenance, repairs, even replacement of a furnace that died. Added up to nearly $100K over some years (spouse died in the early days of C19 [from cancer] and the courts were shut down for months, so it was a long haul to settle this). Survivor got a big chunk paid directly as reimbursement. Executor then split the proceeds among the heirs (of which SS was one of 3, the other 2 being children of a prior marriage). As for basis, I think a lawyer's opinion on the implied life estate is needed before any other determinations can be made. No life estate = basis is FMV when adult daughter died. If there is legal basis to claim life estate, basis = basis on date of transfer, plus daughter's improvements. Ah, these juicy convoluted weird situations people get themselves into.

As I read it, he not inheriting anything at this point in time. The house will be sold on the behalf of mom who is still alive, possibly the funds will be used for her long term care. If the court allows reimbursement for his time, I question as to whether the activity would rise to the level of a trade or business subject to SE tax.

It was nice to wake up this morning to find that the BOI filing deadline has been extended in areas affected by the recent hurricane disasters. FINCEN finally conformed to the IRS extended deadlines, as had been requested weeks ago.

I don't understand enough about how Uber works to tall intelligently about there behind the scenes processes. He was a salesman all his life and really missed the personal interaction when he retired.

I feel you on that. The whole "Check Box" expiring after a year is just baffling. And it seems like a really missed opportunity to actually help people to resolve their issues. It would make way more sense to keep it open for the three year statute of limitations most problems come up after that year. That would remove everyone from having a lot of hassle and confusion.

Love your breakdown of your friend's Uber gig. Right how these cost add up it’s wild. I totally get how the funny money income is not about the mile deduction, because really, it is not! I’m glad he likes driving though! Not always about the money and sometimes it’s just about getting out and meeting people. Have you guys talked about how he could bump up his earnings in busy times or hotspots like that? It’d be nice to hear how it all plays out for him!

Thanks to all for taking the time to respond! This was super helpful.

Seriously, don't guess at this or make assumptions as to how this works. This is a recruiting incentive structured as a loan where it is written off at the end of a designed period if the employee stays with the company. It's an issue that the IRS has challenged because it believes that the "loan" is taxable when given as a compensatory cash advance, and the employer would get the deduction in the year the period ends (in this case, year 3). The complication is exactly how the transaction is set up that will govern when the income is reported. There is case law on this issue also, iirc one of the more recent ones being Morgan Stanley. Here is an older article from The Tax Advisor that discusses the issue and does reference a TAM, but there is more recent case law on this too: https://www.thetaxadviser.com/issues/2011/oct/clinic-story-09.html Here's a blog type article that also describes it and includes some of the advantages and disadvantages of using these employment incentives. https://keepfinancial.com/blog/employee-forgivable-loans-can-be-unforgiving-users-beware The OP should do more research and case law to understand the issue better and not rely on simple, basic answers here as to when it becomes taxable.