graduate admissions - How should I ask for letters of recommendation whose strength is dependent on intended program?

TL;DR I finished bachelor's and master's in mathematical finance but want to pursue pure mathematics, particularly in probability theory. I'm not sure if I should apply directly for a PhD. I might apply for a second master's first.

I think the strength of the letter of recommendation (or whether or not there will be a letter of recommendation) from my professors may depend on the program to which I am applying. How should I ask for a letter in this context?

---

My past questions: 1 2 3 4

---

[Details removed following suggestion in comments]

---

So how might I ask for a letter of recommendation under this context? What I think to ask so far is to first request a consultation asking for advice in applying for graduate programs. At this point I explain I'm not sure if I'm going to apply for a second master's or a PhD. Then of course I ask for a recommendation letter. But how? These are what I have in mind:

Would you be uncomfortable writing me a letter of recommendation?

or

Would you be uncomfortable writing me a letter of recommendation? Would the strength of the letter depend on the program to which I am applying (whether second master's or PhD)?

or

Would you be uncomfortable writing me a letter of recommendation? Would the comfortability of writing the letter depend on the program to which I am applying (whether second master's or PhD)?

or

Would you be uncomfortable writing me a letter of recommendation? Would the strength or comfortability of writing the letter depend on the program to which I am applying (whether second master's or PhD)?

Answer

To me, the following progression seems more natural than either of your suggestions:

I am interested in further studies but I am not sure whether to go to a second masters or a PhD program from here. [Here is my background and here are my career goals.] What are your thoughts?

then

Do you think you could write a strong letter of recommendation for me for [the kind of program you suggested would be best for me]?

and then, if the answer is yes,

If I decide to apply to [the other kind of program], do you think you could write as strong a letter of recommendation for me for that program?