Without going into discussion about keto-enol tautomerism and chemical equilibrium in general (maybe it is not a bad idea you rethink this), if you have any doubts that your compound is in different forms in two TLC samples (commercial and synthesized), you should prepare them in a equivalent way (adjusting pH is easy, if you think might be a problem with your TLC). You could even add a bit of your commercial TLC sample (A) into TLC sample of your crude synthesized product (B) and give it some time to equilibrate. Do TLC of this mix (both commercial and synthesize samples will be in the same solution, thus subjected to the same conditions, thus, should be in the same form) in parallel with A and B (in other words, you should spot A, mix and B independently on TLC, one next to another). After developing and visualizing your TLC plate, you should see one single spot for mix if A and B are the same compound. If you have 2 spots, one with Rf of A and second with Rf of B, you definitely have 2 different compounds. I suggest then you go back to protocol you used for synthesis and see what might have gone wrong.
I can add, that TLC is sensitive method, so Rf values can be affected by admixture of water or other solvents in samples, even in very small amounts. Commercial method of product purification may differ from from what you use. That may be the reason.
Yes, it may be happens, if your crude having some acidic or basic reagent, it may effect on product stability and form another product also. That's why in TLC it may show different spots.