Not speaking from a huge amount of experience here . . . my UDS is fairly new and I assume you are talking about a 28 degree high. Here if it is 28 degrees it is definitely an overnight low. But, the other morning when I lit my UDS, it was 30 degrees and it did not have any trouble at all getting up to 250°.
As long as your drum does not have any leaks, the wind shouldn't bother it either. I would be very surprised if you had any trouble at all.
Brinkmann Smoke 'N Pit with Afterburner
Taylor 1470 Digital Thermometers
Taylor 9842 Instant Read Thermometer