Could applying to too many reaches leave a bad impression on LORs?

[TheLastJedi]

If I apply to only or mostly schools that are likely too ambitious for my profile, and I am willing to accept the risk that I may very well be rejected everywhere – could that make a negative impression on letter of recommendation writers? Maybe I am imagining things, but could it lead them to think of me as a cocky and arrogant person, or become reluctant to write LORs because they feel it’s a waste of time when I’m not going to be accepted anyway?

The reason why I’m suggesting this is because I feel getting a PhD (or any other degree) is a high risk career move – it is in general, but particularly for my situation since I’m an older/mature student, would have to quit my job, and already have a Master’s and therefore can’t get another one on the way.  So I think getting a PhD would be worth it in an ideal situation, but if not it may be too much of a risk and that I’d be better off not going. I don’t mean to sound negative or judgmental, but I’ve seen websites about how graduates of some schools in my field are more likely to get academic jobs than others (and I presume similar trends go for industry), and how some who got PhDs won’t even put it on their resume because it hurt them to appear overqualified. I know people don’t go for PhDs for the money, and I realize there are people who fail at a top school and succeed in a low ranked school. But I feel I need to be confident going into a program or else I might drop out.

It’s possible I may find schools that aren’t highly ranked that I still would want to attend because of the program or research area – but if it turns out that at the end of the day all the schools on my list are reaches, then I want to be able to live with my decision and not purposely look for a low ranked/presumably safer school that I don’t feel confident about attending. My safety would be to just stay at my current job. If I get rejected everywhere and still think I want to go for a PhD, I would reapply the following year. But I don’t know if this would give my recommenders the perception that I’m not a serious applicant.

[SerenityNow!]

I am in a similar situation, have a job that I like but would much rather pursue a PhD and become a professor, and simply told that to my recommenders. They were completely fine with it and agreed with my thinking - in fact they were able to help me come up with a better list of schools based on that knowledge. They recommended a few lower ranked schools that seem to outperform their ranking with their student placements to use as "safety schools" (if there is such a thing in PhD applications...).   

[TakeruK]

I did the same thing as you. All 8 of my schools were in the top 10 list for their respective fields (I applied to two subfields). I didn't want to move all the way to the US for something I could get in Canada, so I only applied to US schools that were better than the best Canadian school (in their subfield).

You just need to talk to your letter writers about your goals and reasoning. My letter writers were also my mentors (i.e. I talked to them about a lot of other academic things prior to asking for letters). So I showed them my list of schools in the early stages and they helped me narrow it down and suggest advisors from places I didn't know about.