I'm relocating for a job next week and I have a few questions regarding PTO and medical appointments that aren't appropriate for my boss or recruiter.

Hi all. I separated from the military in February and am relocating to Maryland to start a contractor position doing intelligence analysis next week. I have 3 questions that I don't think are necessarily appropriate or might be weird to ask my boss or the recruiter:

1.) Since I recently separated, I'll have to go to a few appointments for my medical claim. I also need to see a therapist twice a month, as well as potentially go to physical therapy when possible. During my time in the military having medical appointments wasn't an issue, but I'm a bit worried that having a few appointments a month will be an issue. I'd prefer to not go into detail on the issues, but I know I probably will in order for him to understand the reasoning. How should I bring this up with my boss?

2.) My offer letter states "you will accrue annual leave at a rate of 25 days per year". Based on what my new boss said during our phone interview, I was under the impression that I'd start with 25 days....but does the wording in the offer letter sound to anyone else like I actually will start out with 0 days and earn them as time passes? Because that is what it sounds like to me. I know that this is a question for my boss and recruiter, but it's late so I figured I'd ask here before I email tomorrow.

3.) I actually received/accepted the job offer 2.5 weeks ago, and the recruiter asked if I would need to take any time off in the near future, to which I said no. However this week I found out that I'll need to take 4 days off in November; 2 in the middle of the month and 2 at the end, right before Thanksgiving. I've been told to absolutely NOT use vacation days during your first year at a new job, but also was told that if I really need it, the proper time to bring it up would've been the day I accepted the offer. Like I said, I didn't know I'd need the time when I accepted - I don't have my new boss' contact information, so should I just email the recruiter I've been working with? What do I say? I do kinda bad as it literally just came up, and I originally had no need for days off the rest of the year.

Sorry if these are stupid questions but I'm a bit confused on it all and would love your opinions and advice. Thank you!

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