How many Tourist Visas can an Italian Passport holder obtain within a year for Thailand?

Wrong, 3 times for what?

With multiple back to back tourist visa and visa exempt entries you're more likely be asked to show proof of funds, 20.000 Thb or equivalent in cash, proof of accommodation and onward travel. These are the only things Immigration Officers can ask on entrance.

that's what we are here for

Following the rules => have all your paperwork. No more than 2 land border bounces. Have a decent appearance while crossing (not a rule but good advice), avoid overstay (1 or 2 days not a big deal. I history of 1 or 2 day over stay, or overstay more than 1 or 2 days -- can be an issue). Basically, treat Thailand like a privilege/treat and not right. Be a good tourist.

ooh -- keep in mind crossing the border via land and crossing via air are two different things with different rules. Crossing by land -- you are granted 2 year. By air you do as many as you like (or only 4 a year, I am not sure). Every time you cross a border land or air you are subjected to examination. The border guards look at you, your passport history and decided to let you in or not. Most times if you are following the rules - they will let you in. Sometimes they do not. For that reason I try to cross the border fewer times, and that is why I get the visa. It means I only have to cross the border every 90 days or 4 times a year. By doing the back-to-back via land or air - you will be subjected to examination - 6 times a year. Each time you run the risk of being denied entry. Although, if following the rules - it's less likely.

I usually stay longer than two days. But you have the right idea. I never use agencies. There is some benefit I suppose but I think the further out you go the less common they are. HCMC - Vietinam was a easy to get visa - no need for an Agency. Burma, HK, Korea, Manila -- all easy, no lines, no waiting, no need for agencies.

I believe you can do a land crossing, border-bounce twice a year. That means crossing the border and returning immediately for a 30 days visa exempt. which can be extended 30 days. If more than twice you'll need to get an actual visa.

You should have no problem getting another visa.