Possibly, probably consulate specific but without company history it might be difficult and they may want to see evidence of tax paid. Probably easier to go with one of the soft power options
You're luck they didn't have more questions which could well have cost the visas altogether, but all the people who entered visa exempt and now have a DTV need to print out their visas, leave Thailand, check in to another country and then return to Thailand to activate the visas. You don't particularly need a border bounce company as there should be no issues re-entering Thailand so you may want to look at just hiring a van to take you to the border, wait for you, and take you back
the thai consulate for the country that you are in at the time you apply. Basically you need to treat it as if you were physically attending the consulate, you apply at the consulate and remain in the country until the process completes
that's a different thing. You pay the agencies a lot of money to circumvent the law and still end up having to leave and re-enter. It is not possible for a person to apply for the DTV inside Thailand
You can't apply for it inside Thailand, you can only apply for it at a Thai consulate. Other than that it's a 5 year visa which gets you 180 days every time you enter Thailand
This seems very convoluted. I'd just stick with your current arrangement and keep paying your tax in Thailand. Being able to show tax paid will also help with your application. There's a Dual Tax Agreement between Italy and Thailand so you should be able to claim a credit against Thai tax for tax already paid in Italy. Check the DTA for details