Drug Possession: Charged With Two Separate Incidents of Possession of a Controlled Substance < 1 gram

If someone is charged with PSC PG1 <1g not once, but twice, which is being handled concurrently by the courts, how much more severe will the punishment be?

If they sign for jail time, what could be the possible sentence?
Would getting 1244A be an option?

Drug Possession: Charged With Two Separate Incidents of Possession of a Controlled Substance < 1 gram