I've had a great year, and my tax liabilities will be more this year than any other time by far.

I've also a good friend that is broke, broke, broke.  He does not participate in any relief programs, and basically just works under the table as a lawn maintenance guy.  I know... he didn't play within the system, and now has some issues.  I'm just glad he's not heading down to the welfare office to see what they'd give him.

The issue comes in that he needs cataract surgery.  Both eyes are failing.  He had to cheat his way thru getting his drivers license renewed.  He even admits he's not the safest behind the wheel, but doesn't feel he has any choices.

The cost to get one eye fixed is about $3000, he needs both.  Says he looked into cheaper programs and couldn't really find anything that seemed like a good idea.

I told him I'd pay for one eye.

Is there any way I can use this to my tax advantage?  Would writing a check directly to the doctor be better than directly to him?  I've not bothered my tax lady yet, as there will be a lot going on for me this year.  I've all but accepted that this will not have any upside for me, other than helping out a friend.

No tax advantage. But you can gift anyone you want, a max of $14k a year, without them owing any taxes on it.

Same as if it were your son. You can give him $14k, and so can your wife, for a total of $28k in one year.

Edit: what I would do, is pay for the surgery on my CC, and at least get the points.

If he’s as good of a friend as you say he is, and you’re in a position to do so, I encourage it. Losing your sight is horrible, and it’s a great feeling to help a friend out.

The world will return you the favor one day.

I was kinda having wishful thinking that there might be some tax advantage, so it's not really a disappointment to know there isn't one.

It's funny you say, maybe someday, someone can pay forward to me.  In all honesty, I've lived a very charmed life, where work and intelligence is only a small part of why I've came out OK.  It's really more just being lucky.  So, if I were a karma believing kind of guy, even after this, I still have a lot more to give back.

Going blind would suck.

Only advantage I can think is if you hire him to do some yard work and write it off as an expense. Whether or not he actually does the work you paid him to do would be a civil matter. This wouldn't completely relieve the tax liability, it would only transfer it to him. And it sounds like his tax rate would be much better.

Another thought; I posted a thread a while back pondering using back-door Roth's to "set back" or "push" income in high earning years to lower income years for taxation purposes. It would lock your money away for a few years, but it wouldn't completely tie it up forever like many methods of tax-deferral would. If you can contribute to an IRA to the maximum extent possible, which will offset this year's tax liability, you can then roll it into a Roth (paying taxes when rolled, at the tax rate of that year), and once it has been invested for 5 years you can then withdraw the contributions. This seems like a valid way to "even out" the income fluctuations of small business owners, farmers, etc. Unfortunately, my thread asking about this didn't get any traction and nobody weighed in.