Almost maxed out my Roth IRA, now where do I put my savings?

By now, I've read plenty to scare me into investing as much as possible for retirement as soon as possible. Last year I maxed out my Roth at $4000 (put some of my savings into that, since my income didn't allow pulling from that) and this year I'm already up to $3300 of my $5000 limit. I'm trying to put in $300 a month, which will get me to my limit in a few months.

Ok, so the question is, after I max out my Roth IRA, where do I put my money?

*I am a freelancer so I don't have access to a 401(k).

I'm diversifying my investments away from my Roth right now as the case may be, but I'm not sure if that's the ideal situation. I've got about $1300 in my Sharebuilder (non roth) account which kind of seems foolish. What seems more foolish is my heavy investment in the GLD (gold) ETF, since, despite it making nice gains, is a terrible play for long term. Ok, so I should have researched this before investing in it, but I recently found out that GLD, because it's investing in gold bullion and not the gold mining companies, actually counts as a collectible after a year, which means it gets taxed at 28 percent instead of 15 percent if you hold it long term.

Well, at this point Sharebuilder is starting to seem like a huge rip off. I do like the idea of dollar cost averaging, and I am using up all of my six "free" investments each month, putting $300 a month into my sharebuilder account as well.

My question is... while I could max out my Roth IRA sooner by skipping over my Sharebuilder account altogether, I'm definitely on track to max out my roth one way or another (yeay) and then... what should I do with the rest of my savings? What's the smartest place to put it for growth and tax purposes?

Here are some options I've recently discovered and am considering. Let me know if any sound like a brilliant idea because at this point I'm completely confused.


1) 529 Plan
Part of me wants to go to grad school one day down the line, although I'm not sure of this, and putting savings into a tax advantaged 529 plan would make sense if this were the case. Worst scenerio, one day I probably have kids and they get to take advantage of my 529 plan that never got used, since it can be transferred within the family. Not a bad idea, I guess. Worst, worst case scenerio, I never have kids and someone else in my family gets the money. But this won't help me save for a house/condo, which is really want I want to be saving for right now, as grad school is a maybe and house is a definite sometime in the next 10 years.

2) HSA
I still need to open my HSA account, as my health insurance IS HSA eligible. While I can't withdraw that money until retirement (so it's less flexible than a Roth) I can use it to invest. And there are some tax advantages (that I don't entirely understand) available for the HSA as well.

3) Prosper
I've had great success with Propser in the few months I've been using it thus far. I've only put in $200 and lent to 4 people ($50 each), but the first three at least are paying on time and I'm getting my 8% return, for now anyway. Of course I'll have to pay tax on all that, but it's still a nice return. I just worry about my borrowers defaulting, since one default will take out a huge chunk of the money I'm lending. With $200 in loans, it's not that scary. If I start lending out lots of money, it could get scary.

4) CDs
I already have $12k tied up in CDs that are ending over the next six months. I'm considering putting $5000 of that into my Roth IRA for 2009 when the time comes, but that still leaves $7000 plus whatever savings I manage to make over the year. Where do I put that? Back in a CD? CD and savings rates are so crappy right now (thanks economy!) so it seems like a bad idea for the short term.

5) Put extra savings into my ING Direct high interest savings account and put it into a Roth IRA next year, and the year after, and the year after that. Don't touch it for anything else.

That leaves me with...

6) Keep the money in Sharebuilder and grow my non roth ETF investments. Figure out what the deal is with my GLD investment taxwise and sell before it moves into the higher tax rate. Probably break even on that if it performs as well as it might. Oh boy. What a bad investment! I wanted to hold it long term, but now it seems silly given what a high rate it will be taxed when it take it out. So I plan on focusing my Sharebuilder account on emerging market ETFs. Either they're do awful and I'll lose all that money or over the years they'll do well and with a low fee percentage, I might make some money. It will be taxed when I take it out, sure, but at least it will be a way to grow my savings after my Roth is maxed out. I might sell off my three individual stocks too. I'm a bit confused on dividends, but it seems that if they're going to get taxed each year and then be reinvested and my stocks keep losing money, that's a bad situation for me, no? I don't have that much money invested in individual stocks at the moment (about $300 in three stocks, the largest holding being MCD, and all three of these stocks have gone down since I started investing in them, yet I still owe tax on the dividends).

I like investing in Sharebuilder because it gives me a chance to learn all this. Still, if I want to buy a house one day, I need to be somewhat careful. I know I'm young now and I can take changes, but there's no reason to be stupid about things.

So, faithful readers, help! What should I do with my savings after I max out my Roth IRA?