Over $500k in Personal and Business Credit Card debt: Advise? When should I file?

There are several things you can do.

If your business entity was a corporation or an LLC, ensure that your corporate and LLC formalities are all in order.

Owns up to the problem, which you have already done.

Prioritize your debts by secured and non-secured creditors.

Try to reorganize

Try selling outright, which you said you are trying to do.

Liquidate your assets.

Keep the lines of communication open with your creditors. If the chance of selling is slim then go the liquidation route. After the assets are sold, negotiate with your secured creditors first. If there are funds remaining, then move onto unsecured creditors.

If the enormity of doing this yourself is a burden, save as much cash as you can and seek competent bankruptcy counsel.

 

Legally speaking, You are absolutely correct.

 

With credit already trashed, BK can wait until either something intolerable happens that needs to be undone, or until things are looking up and assets are knocking on the limits of exemption (with creditors still hot on the trail). Any earlier and it's a BK of choice rather than necessity.

BKs destroy judgments (sometimes it takes a year after discharge, but in the meantime the judgment is inoperative). So even if some judgments come down the pike, a later BK will get rid of them.

Remember too that the creditors can file BK on you if they feel it's in their best interests. Involuntary BK would save you the filing fee and the need to do the credit counseling.