You lost *two* ed visas because of leaving without a re-entry permit??
Even with re-entry permits, immigration *do not* like people leaving while they're supposed to be studying. They've been known to deny people entry even with a letter from the school explaining why they're out of country during study time. Especially now; they're cracking down *hard* on Ed visas in a way they didn't before, because Ed visas have been abused so much.
You've now left the country *twice*, when you were here on the understanding that you were here to study. You were lucky to get back in the first time.
About all you can do is what Tod said - and if you get another ed visa, make sure you've learned your lesson regarding leaving the country without a re-entry permit.
Just get the extension. Which you can do weeks and weeks before your expiry date; the extension is added to your *existing* due date, so you don't lose any time. In other words, if your due date is April 1st, then your new due date will be 31st, whether you go in on March 10th or March 31st.
Extension costs 1,900 Baht, one days overstay costs 500 Baht *if you surrender at immigration/the airport and do not have an interaction with police which requires them to look at your passport* (if you get unlucky and/or irresponsible and have such an encounter with police, you get a 5 year blacklisting for even just one days overstay).
So by opting for overstaying instead of getting the extension, you save 400-1,400 Baht *at the most*.
For future reference, if you go for your extension weeks before initial expiry date, you don't lose any days.
The extra 30 days are added to your *existing* due date. So, if your due date is 1st June you still get a new due date of 31st June - no matter how long before your due date you go apply for your extension.
Getting an overstay instead of paying for the extension saves you a grand total of 900 Baht. (1000B for 2 days overstay, 1,900 for the extension).
The risks Brandon outlined above just don't match up with the saving. Just get the extension.
Also, you can go in any time before 29th, as the extension is added to your existing stay (as opposed to the day you went in), so you don't actually lose any days by going in early.
As long as you always get a re-entry permit before you leave, then there are no restrictions on re-entry, as far as I'm aware.
The exception being ed visas. There have been people trying to re-enter on an ed visa, only to be questioned about what they were doing outside Thailand when they were supposed to be studying.
Denied re-entry, even - even with a letter from their school detailing why they were outside the country, and even after the boss of their school was on the phone with the imm officer.
No legal limit. But again, your entry is at the discretion of the immigration officer you're in front of.
Whilst there is indeed no legal limit, the fact that you have a visa does not guarantee you entry, and if you've got, say, two or more back-to-back tourist visas in your passport, the IO is more likely to suspect you of not being a tourist, and you should be prepared to answer questions about what you're doing here.
You're allowed no more than 2 land entries in a calendar year.
The time you spend across the border is irrelevant. Applies whether you're just bouncing straight back, or spending 9 months in that country. The clock resets on New Years Day.