Here is my thoughts if you want to apply to OTS to be a pilot. The next board looks like it is in July, so you have a few months to get everything together. There is/was a board in January, but unless you have already started your application I don’t think you could get everything together to meet the deadline, if it hasn’t already passed.
You can apply to OTS as many times as you remain eligible. There is no penalty and it sounds like you would have a competitive package based on what you have said on the leadership side. The Air Force cares about your pilot abilities also, but there is a wide variance of people applying from people with 0 (zero) hours to thousands of hours. You can work on your ATP while applying for OTS. The payback in the Air Force may be longer. As a brand new 2nd Lt you would be making $3,034 per month or $36,408 per year for the first 2 years plus your flight pay which is another $125 per month for the first 2 years of flying. You do get a promotion to 1st Lt at 2 years and then another to Captain at 4 years, so your pay does eventually go up, but even as a Capt at 4 years you are making $5,398 in base pay plush $206 per month in flight pay, so $67,000+ per year. My point is that is a lot of money up front and you just need to be aware that it will take a while to pay back. Of course I haven’t done the comparison to regional pay for the first 4 years of commercial flying, so maybe it isn’t that different. In the long term, the pay difference is much greater between the military and commercial flying. At the 22 year point in the military as a Colonel (O-6), my pay is $123,825 annually plus $840 per month in flight pay (it actually starts to decrease at the 22 year point to $540 per month, but I started flying late in the Air Force).
Having the ATP doesn’t “hurt” your chances, but you are correct that it is a $65,000 question of how valuable the military sees it. The military and civilian rules are very similar overall, so it would be helpful in learning and knowing the rules going in to pilot training. The difference is you would be flying the T-6 and then the T-38 or T-1, so pulling Gs, faster airspeeds, and more complex aircraft than a single engine Cessna or even a twin. The military rules that are different are usually while we are in a restricted airspace, MOA, combat, or other places, otherwise when we fly in civilian airspace we follow civilian rules and use civilian controllers (& military controllers often control civilian traffic).
So my main point is I wouldn’t delay applying. Apply now (for July board), see if you get selected, if not then continue to apply while you also look at guard, reserve, and commercial options. There are commercial pilots that join the guard or reserve and take a leave of absence from their airline job but keep their seniority number (not sure if they have to return to the airlines in 5 or 7 years). If ATP makes sense and you know the military pay vs. regional pay differences and are confident that it makes financial sense then you can make that decision. Every OTS board you skip applying is giving you a zero % chance of getting selected and you never know how competitive each board is going to be. Yes, the military is competitive, but when the economy is good and the airlines are hiring our recruiting numbers do tend to decrease. You can continue to put in an application every six months or so until you get to about 28 1/2 years old.
Always good to aim for your primary goal and have 1-2 backups. I don’t think you can go wrong with any of the 3 options you are trying for.
Hopefully that was helpful. Glad to answer any more military specific questions for you.