You cannot transfer the regular account shares into a Roth, only those in an IRA.

Yes, you must wait 5 years from the transfer, but you wouldn't take out funds from a regular IRA until age 59.5 anyway.

My thought is that it is not worth waiting, as you can start the five year clock running, and you can do a recharacterization (reverse the conversion) until October 15 of the year after conversion to give you time to see that things are going well.

For me it works well, as I cannot contribute to a Roth due to income limits, but there is no limit on doing a conversion and it makes sense with depreciated assets. You got the deduction for the original IRA contribution, and only have to report as income the value at the time of transfer (not on the original basis). I can't tell you if your broker will use the last trade price or the current zero value, but obviously the zero value would be a real potential windfall.