When claiming insolvency, should I contact a CPA? Has anyone done it on their own?

[DanielV01]

It depends.  Insolvency can be a difficult calculation.  At TurboTax we are in the business of self-preparation, but we do recognize there are times you may have a complicated situation.  We have a service available, TurboTax Live, that can give you this type of assistance with a CPA or an Enrolled Agent, and maybe even a tax attorney.  One caveat, however, is that we are very close to the filing deadline.  I will provide you the FAQ regarding this service, but you may want to file an extension as a precautionary measure, because while TurboTax Live will be available after April 15th, they might not be able to assist you before April 15th to file on time without the extension.

Here's the FAQ regarding TurboTax Live:  https://ttlc.intuit.com/replies/6071042