I have been lurking here and reading through the MMM articles for the past month. Prior to discovering this site, I had resigned myself to thinking that I would be retiring no sooner than age 59.5 (I am in my mid twenties). Now that I have a new perspective, I am questioning my previous strategy of maxing out my tax advantaged retirement accounts before even thinking about taxable accounts. My employer has a SIMPLE IRA plan that matches my contributions up to 3% of my salary and I can max out my contributions at $12,000 per year. This account has basically the same rules as a traditional IRA (contributions deducted from taxable gross income; withdrawals are heavily penalized prior to age 59.5; withdrawals will be taxed). I am also currently contributing biweekly to fully fund my Roth IRA. Also, I have overfunded my emergency fund and I plan to invest about $30,000 of it very soon. I have all of my investments in Vanguard's Target Retirement 2045 fund right now, and I plan to purchase the underlying funds of this fund once I can purchase admiral shares.
My current plan is to continue fully funding my Roth, use $5,500 of the $30,000 to fund my wife's Roth, and leave the rest invested in admiral shares of Vanguard total market index funds in a taxable account.
My questions:
1. Should I stop contributing to my SIMPLE IRA beyond 3% of my salary and instead put that money into a taxable account?
2. Should I continue fully funding both my and my wife's Roth IRAs if our goal is to reach FI in our 40's ( knowing I can withdraw principal without penalty)?
3. Should I try to time the market when investing the $30,000 since it is at an all-time high (or use dollar cost averaging or some other strategy)?
4. Will my investments be converted to admiral shares if I have a total of $10,000 of a fund held between my taxable and IRA accounts, or only if I have $10,000 of a fund in a given account?