Will I be able to choose my work release start date in Colorado?

It will depend on the Judge and the County. Sometimes a judge will allow some leeway in choosing a date to begin a sentence, but I've never seen flexibility beyond a week or two. If you're hoping to move your start date further than that, i would not count on it. In addition, there are a number of judges who expect Defendants to begin serving their sentences on the day of sentencing, and will take you into custody on that date. If you don't have an attorney, try and speak with the public defender in your courtroom and ask about the judge's policies. Good luck.

It is POSSIBLE that the priors may not come into play at all. I would be happy to discuss this with you further if you would like.

Your post states that you're from Colorado Springs. As no one from Colorado Springs has answered yet, I'll weigh in. Almost all El Paso County judges will give you leeway up to two weeks after sentencing for almost any reasonably good reason. Most judges will be open to a stay of execution beyond two weeks for a VERY good reason. I don't know what business you are in, but I've negotiated a long stay of execution on a work release sentence (on a third DUI no less) for someone in the construction business who wanted to start after the busy summer season. Other reasons for which I've been able to work out long stays include accommodation of military service, school schedules, and tax season. Additionally, I agree that older cases out of state may or may not affect you. You should talk to an attorney about that further, especially in light of the difference between a first and a third DUI. In any case, the DMV will not count your out of state priors against you for DL purposes.

The judge has discretion whether to give you a stay from the time of sentencing. Most of our local judges will give a short stay, but waiting for a business's slow season is not likely. If you are pleading guilty, you can have some say on your sentencing date by which court date you agree to a plea. If you already lost at trial, you might not have a choice. Bottom line is you need a lawyer to handle this. Many people do not realize they have a defense when they handle it on their own. And unless you have already made a plea agreement, you do not know how much jail time you are actually going to end up with.