That is unfortunate that your condo has gone down in value. Are you talking about a residential condo?
Here are some current prices for medical condos in the Southern California Area (per square foot):
Beverly Hills: $800s
Irvine: $500s
Foothill Ranch: $300s
San Marcos: $400s
These are all higher than they were 5 years ago, even 2 years ago.
Home prices fluctuate greatly for many reasons I won't get into, but well chosen commercial property is not going to decrease in price.
This is true because of supply and demand. There are hundreds to several thousands of students graduating from medical school every year and they will ultimately need office space.
Since you have a lot of experience with residential I will use that as an example:
Home prices in Southern California have dropped approximately 20% from last year. However, in downtown Los Angeles they have not dropped because there is no more land to build in downtown Los Angeles and there are people who need to live downtown for their jobs. So the price stays the same.
In Beverly Hills they have created a moratorium on converting or building medical office buildings in the city. This caused prices to jumped $200/sft over the last year.
I am not a financial advisor. I am a medical real estate developer. I've put hundreds of doctors into my buildings over the last 10 years and not one of them has failed and not one of them has lost their money, even right now. Why? (There is no magic and there are several other successful developers that can make the same claim) Because I build medical offices where doctors want to be, not where I want them to be, so the value increases. Whether you can pull money out of a Roth IRA to by a first home or for educational expenses is not really the point, in my opinion.
The point is that you can't buy medical office space with your Roth IRA. I have watched many people lose a lot of money on stock investments, which is about the only chance you have of keeping up with real estate.
This is why I love it when the stock market gets loopy like it has over the past several months: it keeps my cap rates low because every investor is unsure of what the stock market is doing comes running over to real estate.
BTW, you can do a 1031 exchange into a investment property. Instead of selling your residential condo and buying a new one, I would suggest you think about selling your residential condo and buying a small medical condo with an existing tenant who is making good income. In your case a 1031 exchange wouldn't be helpful if it is true you are upside-down. A 1031 exchange is meant to protect your taxable profits. Nonetheless, I would still suggest you think about it.
And that is what I would again, recommend Laker thinks about. Medical office space is far more stable than any home investment.