You need to send a copy of your passport and the VO will know by which status you have entered, how you changed, how many times you had travelled etc.
But, I dont' see any issue with changing the visa status legally. Just provide enough documentation related to each stage if you can. I personally have changed status from H4 --> H1 --> GC. My parents were not asked such questions related to 'why your daughter changed so many visas?' etc. They were granted 10-yr multiple entry visa.
I was also B2 --->F1-->H1. I received my first H1 stamp in Toronto in 2001. You should mostly be fine if you completed the degree for which you changed to F1. If you did not complete the degree for which you changed to F1 your chances are very low to get the stamping.
Make sure you takje degree certificate that you completed. Also if possible take original F1 approval by INS (I 94 witrh stamp showing change from B to F visa).
Best of luck
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