Boss crossing work at home boundaries

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I have worked with my current employer 10+ years and am at our maximum PTO accrual rate of 5 weeks/year. I've been looking at changing companies and have interviewed with a few. When I talk to HR, they often tell me the benefits package and note that I'd start, as a new employee, at the bottom rung of PTO accrual (often 2 weeks). Is this often negotiable? Is it unreasonable to think that the same years of experience that make me a good fit for a role should also qualify me for the higher PTO accrual rate? I realize I may not get all the way to where I am today, but to go from 5 to 2 is a kick in the gut.

I submitted two R&Rs to two different recruiters for the same contract job. The first recruiter, I don't know if he submitted my R&R, and they told me he is on vacation for three weeks. Another recruiter called me for the same job, and I did not mention I worked with another recruiter. I don't know how this process works in contracting roles or if I should let the new recruiter know. I'm worried that if I say something about working with another recruiter he may not work with me, but if I don't say something, my R&R may actually go through and I get the job. I'm really not sure how to proceed here. advice ?

Would this be appropriate, or should it be sent from a personal email account instead? Thank you in advance!

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My job has a lot of ebbs and flows. The busy season is almost upon us, but right now I have absolutely nothing to do. I am so bored all day long. When I'm bored like this, I usually start looking for new jobs. I have to be challenged to be content. But I really enjoy my boss, and I'm trying to stay here for at least another year or two. Last time I experienced down time, I subscribed to Coursera and got a certificate. Right now, I spend a lot of time on LinkedIn. I don't really have funds (personal or professional development through work) to do anything that has a significant cost. Does anyone have recommendations on what I should do?