Your first question is whether you can have 2 loans outstanding at one time. The maximum number of loans permitted in a plan is an optional feature, meaning your plan dictates the answer to this. The most common number of loans you have have in a plan is 1 or 2, but the only way to know this for your plan is to check with your plan administrator or read the summary plan description which will contain the answer.

As for the tax penalty, not all IRAs will take an outstanding loan. It is very likely that when you rollover to an IRA your outstanding loans will be treated as a taxable distribution. In that case you would pay taxes and a 10% penalty when you file your tax return. Check with the institution that you are rolling into to see how they handle outstanding loans.

You can normally have only one loan from your 401(K). It's better to withdraw from the IRA before the tax penalty if you're really hard up. You'll take the tax penalty, but if you can recoup the money, just make extra contributions to the 401(K). Check with the firm or broker that manages both of your plans to get the specifics about what you can or can't do with these plans.

If your IRA is a Roth, it's worth remembering that you can withdraw contributions, but not earnings. This means you could theoretically tap it for money before the rollover. Under the Roth guidelines, you wouldn't even incur a tax penalty.

Always try to withdraw as little money as possible from your retirement accounts. You're losing valuable money and time to grow it every time a loan is taken out.