He said I would save $5-6k in taxes, but man, I don't think it's worth it. It has made my accounting so much more difficult.
It should save more than $5K or $6K. Probably double that unless you're in CA.
Also, it hasn't really made your accounting more difficult... unless you simply haven't been doing your accounting.
The thing you need to do, probably, is outsource your payroll. Spend the $1000 or whatever to have a full service payroll solution. That payroll burden and then the S corp tax return represent the only extra work of having an S corporation.
It has most distressingly caused a nightmare in that I cannot seem to get payroll to work. I started the process but then ran into a problem with the payroll provider. Then I ran into a problem with my state's department of tax. Then it was another thing. And another thing.
S corps often stress someone the first few months and year. You're setting up the payroll which is often a new thing. And then you're learning to do "real" accounting often (since that's required for the actual S corporation return). But these are really just learning curve issues.
Also this note: Unless you decide to never grow beyond a one person operation, you will have some point have to set up a payroll system to deal with that first (and any subsequent) employees.
I know, no excuses. I had a phone call with my accountant today and he advised of two options:
1. Suck it up, sign up for payroll, and pay myself my yearly salary over the next three months. This would make cash flow tight but I could probably do it.
Two hacks for making the payroll situation easier this year. First, be sure to correctly report your health insurance as wages. That'll give you a chunk of wages to report on your S corp tax return...
E.g., if you have $10K of health insurance, do the accounting right and that'll create $10K of wages but wages that aren't subject to income taxes or payroll taxes.
Second, probably you can do a third quarter payroll tax return that looks back at July, August and Sept and says, in effect, hey that first $16K I paid out to myself? Yeah, let's call that $16K payroll and report on the third quarter 941 return due in roughly a month. That'll trigger $2448 of federal payroll taxes. But that deposit can be made in roughly a month with the 941 return because it's considered "de minimis."
Then whatever else you need you can deal with in the fourth quarter. But you'll have a head start...Using the examples above, you might have a $26K head start with $10K of health insurance an $16K from the third quarter.
2. Quoting here: "One thing you can consider doing is simply giving yourself a 1099 for $36,000 instead of doing payroll. You would be running the risk of getting audited for it, but it is something that a few of our customers do because they don't want to deal with payroll and they are willing to take the chance." He went on to advise of a bunch of caveats and that I'm exposing myself to audit.
People do the above... But I think it's a bad idea given you still have time to do this correctly and in process get your payroll set up.
BTW, to provide context for my remarks, I have prepared thousands of S corporation returns...
P.S. You might find my S corporation FAQ useful:
http://www.scorporationsexplained.com/scorpexplained-faq.htmand we've got quite a bit of S corporation info at our blog:
https://evergreensmallbusiness.com/?s=s+corporation