You would be given another 60 days upon entry, however this is at the discretion of the immigration officer when you enter Thailand. So your history here will determine if you will be allowed back in on visa exempt.
However you can get an extension of 30 days (if you haven't already) at your local immigration office for 1900 and some paperwork
I transfer over 100k a month into thailand without issue and have for nearly 3 years. I had one issue where it took over a week to arrive as they requested proof of where the money came from (I didn't see the email and the notification didnt push through) a year and a half ago and since then the money is in my account every transfer within 3 days. WU blocked me and returned ฿15k to my UK bank 4 weeks after the initial transfer and all 3 of my UK banks can take anywhere from 3 days to 4 weeks to complete the transfer.
a lot of countries have automated gates now. It's down to the person to make sure they know the rules and when to leave. If someone ends up overstaying they only have themselves to blame. It's not hard to calculate dates and set reminders
Your airline is the one likely to give you problems. Best to speak to them about their policies on non-visa travel. You don't have a history in thailand so it's extremely unlikely immigration will give you any problems or even ask you a single question.
you need to have a statement that shows an 11k balance per month + a month salary deposit (so savings of 11k (and not dropping below that 11k + salary deposit if using the remote work instead of soft power) example Jan 11k + salary, Feb 11k + salary Mar 11k + salary etc etc.
it is technically cheating the system, you do not have the money and are borrowing it to met the requirements and returning it after visa is granted. Most embassies are now increasingly requesting months of bank statements for this exact reason.
visa validity period doesn't mean shit mate. Having a visa does not guarantee you entry into the country. You can be asked at anytime by immigration to show you still meet the requirements of said visa. If you are unable to show what they request or no longer meet those requirements on which the visa was granted they can deny your entry and even void your visa under certain circumstances.