Thanks so much for all of your advice. This was my first time posting a question on the forum and I'm very happy I did. I called Fidelity and spoke to a representative that seemed to be a bit more versed in the policy details. Apparently, a "life event" can include simply "retiring" and then I could transfer that money into a traditional IRA and then over to a Roth IRA when my income is lower. I did do some initial calculations below on merits of an LLC vs. sole proprietor if I considered $100k in 1099 income and filing as an S Corp claiming $60k in W2 income.
Sole Proprietor:
$100k income
$18,000 in employee 401k contribution
$18,547 in employer contribution
Total 401k Contribution: $36,547
15.3% employer tax on $100k-$36,547 = $63,453 * 15.3% = so $9,708 (have to pay all other taxes regardless so just focusing on payroll since my 1099 work is basically all W2 in reality)
LLC filed as S Corp:
$100k income - $60k as W2 (using internet salary justifications of "reasonable" salary for my type of work)
$18,000 in employee 401k contribution
$15,000 in employer contributions (25% of 60k)
Total 401k contributions: $33,000
15.3% employer tax on $60,000 - $33,000 (assuming I deduct out 401k contributions from W2 right?) = $27,000 * 15.3% = $4,131
LLC establishment fee = $225
Corporate tax filing = $1,500 (anyone have a cheaper accountant or even one that doesn't charge $200/hour to answer questions)?
Payroll = $100/month (if I have someone else do it) so $1,200
So while it looks like I save $5,577 in taxes by filing as an S Corp, I would incur $2,925 in fees to operate so only save about $2,652 in taxes, but would obviously increase my audit risk. I'd be able to stash away a bit more as a sole proprietor as well. Am I thinking about this correctly? What else am I leaving out? Is there any justification based on my scenario above to risk going the LLC route?