Hello,
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Item 1
What I am looking to understand, is the likelihood that the prosecutor will/will-not grant me a second extension. In general, is granting of such a request 'rare'?
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Typically a continuance is granted the first time without any real reason necessary. A second continuance is a little harder to get, but is usually granted if the defendant explains that they have approached several attorneys and are close to having the money to hire one. As a former public defender, it wasn't really that uncommon for several continuances to be granted in low level cases. So no, it isn't particularly rare for a prosecutor to agree to a second continuance.
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Item 2
If the prosecutor does not grant the extension, do I have any options to achieve a similar goal (delay so I have time to obtain an attorney).
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Yes, you simply plead not guilty and request a trial date which is typically several months off.
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Item 3
If I do not receive a continuance, and no other options exist to provide the time I need to obtain an attorney, I need to determine the course of action with the least amount of (potential) risk. If I were to plead not-guilty, how aggressive do prosecutors generally pursue such cases?
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They don't aggressively pursue cases like this. They aren't going to get mad if you plead not guilty. These type of cases are more of an inconvenience to the prosecutor as they could conceivably take up a half day of their time if it actually went to trial and they much prefer to settle them rather than have to go through the time and effort to prepare for a trial like this.

In my instance, I have no criminal background (not a repeat offender, etc). To a certain extent, pleading not guilty would provide me the time needed to obtain an attorney, but I'm concerned at that point I may have set myself up for failure as I have already delivered my plea. I understand you can't determine how aggressive my particular prosecutor will pursue, but in general, how much effort is placed to obtain a guilty verdict (witnesses, evidence, etc) for a Misdemeanor assault charge?
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In a case like this, if it is set for trial, it will typically be a few months out. The prosecutor won't even start doing anything in preparation for the trial until about 3 weeks away other than contacting any witnesses to make sure he can get in contact with them about a week before trial.
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Further, you can always change your plea at any time if you change your mind and the original offer will still be there. Actually, in my experience of handling literally hundreds of cases like this, the offer gets better the closer to trial because prosecutors hate to try a case like this with questionable facts as it means other cases have to get backed up while they work on this one.
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So worst case scenario, you plead not guilty, get a trial date a few months off, get an attorney, and then change your plea if he doesn't feel you have a good case and accept the disorderly offer.
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Thanks.

Barrister

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