Let's say a person is making regular monthly contributions to his/her Roth IRA, HSA, and 401K with employer match, up to annual limits. All contributions are put into index funds. Assuming this person is able to, is it ever a good idea to max out the accounts earlier in the year? Essentially, the Roth IRA and HSA would be maxed by March, and the 401K would have just the right amount in it to where smaller contributions in the remaining 9 months are only made to get the company match.
The strength of your plan is that you have considered that if you contribute early the the 401K you might not get the match, so you do stretch it out for the entire year..
One benefit to putting money into the HSA early is that it will be available if you need it early in the year if you have a major medical emergency in the first quarter. If you need to pay a $4,000 deductible in January because of Appendicitis you would hate to have to use post tax money to pay the bill. Of course If you have had the HSA for several years then this might not be a problem.
If you haven't maxed the Roth IRA for 2013, you could make contributions to the IRA up until April 15 2014 to count for the previous year.
A risk with the HSA is if you leave your employer mid-year. You can keep the money, and use it for medical expenses, but if the new company doesn't have a an HSA/High Deductible plan you might have contributed too much.
The 401K, HSA, and IRA are annual limits. So if you will switch companies you are responsible for not going over the limit.