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>>I contribute to the UC 403b pretax equity (indexed) fund. The university does not match any of my
contributions (There is a separate Pension plan). I am at least 20 years from retirement age.

1- Under what circumstances does it make better sense to do a Roth IRA?<<

If the investments available in your 403b significantly underpreform the market or if you are an aggressive investor, then you may be better choosing a Roth IRA where you can select investments that meet your style.

You should also look at which option will give you the highest after tax cashflow when you retire. Assuming the same investment returns, the 403b will grow faster because you can contribute perhaps $3000 pretax to the 403b compared to $2000 after tax to the Roth, depending upon your tax rates. Even paying taxes on the 403b money on retirement, you may (or may not) have more cash after taxes than with the Roth with no taxes. Again depends on tax rates.


>>2- We have some home improvement projects we'd like to do in the next 1-5 years. We can
borrow from the 403b, paying ~7-8% interest (most of this back to our account). The payments
are with after-tax dollars, so this money would ultimately get taxed twice once it is finally
distributed. Does this have any advantages compared to<<

The advantage is that this is a very low cost loan to you. But it is not tax deductable even though you are using it for home repairs. Also if you fail to pay it back in the allotted time, then the IRS will treat it as a premature distribution and you will owe a 10% penalty and taxes.

>>a) Building up a war chest with after tax dollars? (unfortunately, the chest doesn't have much in it
right now so we may be forced to the 403b-loan route, or b, c below for some of our more
pressing projects)<<

Always a good option. Nothing wrong with waiting until you can afford to buy something and eliminates interest costs.

>>b) getting a home equity loan?<<

This should be tax deductable and depending on the terms of the loan, you may be able to roll it into your mortgage in the future if you refinance.

>>c) getting a regular bank loan?<<

In my view the worst option. Not tax deductable, but if short term until you can refinance your mortgage, it might be alright, if you can get a low interest rate.

One option you haven't listed is refinancing your mortgage to take out cash and using the cash for the improvements.

>>3- We have young children we would like to put thru college starting in ~14 years. What's a good
way to start saving? Roth? 403B loan? other?<<

I shouldn't even try to answer this question because both my kids have 4 legs and do not much chance of making it into college. Find out about the educational Roth. I don't know much about it. I'm not in favor of touching 403b funds as I consider this part of my retirement nest egg. A very conservative investment would be US Savings Bonds. Rates are low not much more than inflation. But under the right conditions, there are no taxes on the interest if used for education.
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