Tax ourselves a little at a time or at end of year?

AGREED! Ridgeline must have the worst CPA on earth if he's paying 1/3 of his gross in taxes!

 

So your also paying state and federal unemployment taxes? You could theoretically fire yourself without cause and collect unemployment lol. But unemployment now is only available due to termination that you cannot control therefore you could not collect unemployment cause you terminated yourself.

One thing to take into account is what cost most the penalty for not paying quarterly or the unemployment tax. I'm not sure the exact rate of either one.

Another way to pay yourself through a llc or a s Corp would be a minimal amount in the form of wages pay the max available perdiem rate you can till uncle sam starts taxing it I think it's like $63 a day for 2018. By going the per diem route the s Corp/LLC treat the per diem as a write off and only 20% is taxable on the employee side of things both income and fica. If you go with paying yourself a W-2 wage this is the best route it will however lower you social security benefit down the line. I'd suggest setting yourself up a company provided IRA or 401K and give yourself a very generous match for your retirement plan.

There are some very creative ways you could reap benefits down the line through paying yourself through your own llc/s Corp payroll

 

Unemployment insurance is not available for sole member of an S Corporation in Oregon. Thus, I don't pay into it, neither can I collect it.

Yes, I do utilize per diem as part of my salary structure.

And of course I have a SEP set up.

As far as being concerned about S.S. benefits being effected by per diem, etc, I've been self-employed in one way or another most of my working life. Thus, paying into the system.

I'm 61 now and my benefits pay out is pretty well established. You can sign up on S.S. administration and actually look at all your contributions over the years. They also provide a chart that shows what your monthly benefit will be if you take early retirement vs maxed.