I didn't say you're "entitled" to enter. I said it doesn't matter how you enter. There's no requirement or expectation that you're entering from any location, via method, on any date. You can do whatever you want and it makes no difference in regards to your visa for entry purposes.
I don't have this experience as my company is publicly listed, but this is by far the most difficult requirement for the vast majority of people who want to apply for this visa. Many privately held companies simply will not release this information.
There is no rule that says you cannot do that, but do know that there are MANY reports of people getting pulled out of line at the airport and grilled for an hour about why they are back so soon after just spending 90 days in Thailand. After 90 days they are looking at you suspiciously as that's not the normal behavior of a tourist. You probably won't be denied entry for your 2nd entry, but they might warn you that it's your last time entering without a long-term visa.
Unless you were married when the child was born and have your name on the birth certificate, you don't have any legal parental rights. You would need to go through family court in Thailand in order to be recognized as the father.
You MIGHT be able to get the 90-day non-O visa for visiting a Thai family member based on your daughter. It depends on if the embassy will only recognize the birth certificate even if you're not recognized as the father.
But without parental rights and custody, you won't be able to get an extension inside of Thailand based on having a daughter. So you'll be limited to 90-days from the visa (if you can get it) before you have to leave.
Why are you applying for a visa now if you plan to move in November? You're going to be wasting many months of the visa. Once you're approved you only have a limited amount of time to obtain the visa before the approval letter expires. And you cannot get the visa without the insurance.
And the non-OA insurance has nothing to do with LTR. The non-OA has a $100,000 minimum and must be from a specific list of Thai insurance carriers. The LTR insurance does not have to be that much and also does not have to be from that list.