I handed only my passport over for my last report, but it depends on Immigration Office, some want you to fill in the application form, a copy of your notification of address.
The Re-Entry permit cost 1,000 Thb but is only valid until the Admitted until date stamped in your passport.
As you are not sure if you can make it back into Thailand before that date I would advice, just leave and apply for a new Non O visa before your next trip to Thailand.
Last three months before application, you wrote you will be employed 9 months when you need to apply, gives you time enough to meet the requirements of last three months before application date.
You can use salary made in Thailand, you need to show proof of 3 months prior application date payments of tax and sso from you and the Thai staff members.
Also copies of work permit.
Ask your local Immigration Office for the hand out with requirements to make sure you meet them all.
Walk into an Immigration Office with your passport, explain why you want to stay longer than allowed and how long you like to stay. Ask them the possibities to obtain a legal stay for that period.
Only options available is:
60 Days Extension of Stay based on visiting family (if you're married of has children)
60 Day Extension of Stay based on being unable to travel
Application denied and 7 days to leave the country.
Yes, you an apply. But be aware countries are opening up, International airports in Thailand are being used to leave Thailand and on top of all, land borders are also open to leave. But you can always try to explain why you can not travel in the next few months.