Hmm I am in a similar situation. I am an Army O, RW pilot. If all goes as I dream, I will be out in 4 years, 10 months, putting me at 29 1/2, almost 30 years old. I want to transition directly into the ANG to fly fast movers, so if the stars align and my dream works out I will have been hired by the ANG unit by then and perhaps have a UPT slot. That is pushing it real close...probably too close. I was told, however, that I would be going to an abbreviated UPT. I do not know all that much about that scenario, but I was wondering if the age limit still applies to this "abbreviated UPT" that I was told about?
As for the Army I know a guy who was 31 in flight school...a CPT. I also knew some older WOs. Those waivers depend on the unit if NG/reserve and needs of the army for AD. There isn't nearly as much demand for an older commissioned officer (generally a branch transfer CPT) whose timeline requires a company command fairly shortly after flight school because the officer has very little aviation experience and couldn't command a company as well as someone who knew aviation better. If it is a newly commissioned O, good luck getting an age waiver in active duty. There are plenty of qualified younger LTs and not enough aviations slots to go around as it is.
I have seen some fairly old prior service folks become WOs. Just depends on needs of the army. And, if you could get hired by a NG/Res fixed wing unit, I'm certain a waiver could be attained if they wanted you if you did decide to check out the army.