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In response to your questions

1. I don't believe that you can mix multiple rollovers into a single IRA rollover, but I would check with the custodian where you wish to set up the rollover. Since EGTRRA (2001) there is really very little reason to designate a TIRA rollover, unless an employer's plan will somehow not accept a TIRA rollovers to its plan, as they must be accounted for separately.

2. You may continue contributing, as a SEP or SIMPLE transfer should have nothing to do with your plan eligiblility.

3. The major con is that if you do a SIMPLE rollover to your IRA within the first 2 years of having contributed to the plan, there will be a 25% penalty. You may transfer to another SIRA without the penalty, which sounds like what you are trying to do with Vanguard. But a pro to doing this (after the 2 year waiting period) is that often SIRA's have higher annual fees that a TIRA, but this varies by custodian.

It sounds like you are not fully engaged with your regular contributions and the mandatory match of your employer. Don't you get a monthly earnings statement that shows things like fed/state and FICA withholdings? On it should be the amount you agreed to have deferred from your salary to your SIRA along with the employer match (although in some cases, the match may be delayed). But I'm not sure what this has to do with your accountant. The amount on your W2 in block one should be your salary minus contributions to your retirement plan (and perhaps minus other salary deferrals you might have, like an HSA or FSA). And why do you think the $$ sitting in your current SIRA account is 'potentially disasterous'? Remember, all SIRA contributions and matching are immediately vested to you and therefore belong to you, not the employer.

A good place to go to ask IRA specific questions is Ed Slott's site at
http://www.irahelp.com/cgi-bin/forum/index.cgi . You have to register, but its free. And there are a couple of accountants over there who seem to know a lot about SIMPLEs, SEPs and TIRA's.

BruceM
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