Even if you owned a resort outside of Thailand I think they'd worry about you contacting possible Thai clients. Sounds like you gave them way too much info.
hope for the best, you have 2 days. I may be wrong but, if for instance the money is a day late you might be able to pay the overstay fine and complete the extension.
The money has to season for a full 2 months date to date. On that day you can go to immigration and apply for your one year extension. What date is your current permission to stay stamp? No health insurance or background check requirement, insurance is always a good idea though. You need to make sure that the TM30 has been filed by your landlord, check with your local immigration office to see if they want to see your lease when getting the extension. You'll need the residence certificate from immigration if you want to buy or sell a motorcycle or get a Thai driver's license etc, they're good for 30 days.