there is no rule to say you cannot, however if you keep getting too many tourist visas at the same embassy/consulate they will start to red stamp your pp
in order to do the conversion from a 30 day visa exempt entry or a 60 day tourist visa entry to a 90 day Non-B visa you need at least 15 days left on your current stamp. That's because the application goes under consideration for 14 days before you go back get the Non-B visa and the new 90 day stamp inked into your passport.
You can convert a tourist visa to a Non Imm B visa at your local immigration office along with all the required documents from your employer without leaving Thailand
Perhaps but I cannot help but notice the amount of people being taken to the side when entering the country and interviewed regarding the amount of entries in a specific time frame. More and more people are being denied you only have to look on this group for examples. As well as what you mentioned the proofs and onward travel ticket. Ultimately it is down to the individual IO so there is some luck involved too.