This is interesting because I have a similar issue. I'm about to starting using a new CPA and I want to ensure he's not steering me wrong. I'm a single member LLC which was established 01/01/2019 and my (new) CPA is filing a late s-corp election request to be effective 01/01/2019. Before I connected with this CPA I was on a hunt to find a payroll company that even would file a 2019 payroll since my (old) cpa was "too bogged down" to do my payroll for 2019 (we have since "parted ways"). It took me four tries to find a company who would do a 2019 payroll this late in the game. So, when I came across this new CPA to do the taxes for 2019 he advised me to stop my 2019 payroll plan with Paychex and not pay any wages to myself in 2019. That would mean around $150k would go to me as a shareholder distribution wherein, normally, $60,000 would have been payroll. When I inquired as to the reasoning (and legality) behind this his exact words (email) were,
"The IRS allows late election S-Corp as far back as 3 years as long as you have the LLC in place. The requirement that I’ve used with all my clients is starting payroll moving forward and not going back and doing late payroll that will cost late payroll tax filings and penalties. My experience and relationships with other CPAs is that you start the payroll moving forward and the IRS will not bother you as long as you do it moving forward. I have done that with dozens of clients who got 3 years of payroll taxes cleared by going back and doing the late-election."
I mean it sounds fantastic but I'm wondering how "normal" this is. The intent was never to "dodge" payroll taxes for 2019. My old CPA misinformed me (fired him) about whether or not I could elect an s-corp and so it just never happened. That said, COVID is hurting me. All this money we're supposed to get is taking so long to roll in I'm going to have to do something quick. This tax break could be a huge help but the ends don't justify the means. I just don't know how normal it is to go, "Well, I wasn't an S-corp last year and it got approved so I'll just do payroll for this year going forward."