AS you are not allowed to be longer than 90 days inside the country, you normally do not have to make 90 days reports.
BUT some Immigration Officers start telling the foreigners to make 90 days reports as they seem to be very long times inside Thailand based on the fact that they are unable to travel.
With not knowing where you are, the only option you have is to visit your local Immigration Office and ask them if they want you to make the reports and when you have to do this.
For the conversion into the Non Immigrant O visa there is NO seasoning of the money required.
For application of the 1 year Extension of Stay the money must be at least 2 months in a Thai bank account.
As the are named the same, retirement visa, the conversion into a visa and later an application for 1 year Extension of Stay are two total different ways of stay with different rules, regulations and requirements.
There is no official limit on how many times a person can apply for a visa.
Neighbor countries did stamp visa in the past that the person does not get another tourist visa at that Embassy after 4 or more back to back visa applications.
Get a visa that fits your purpose of living inside Thailand, do not use the short term tourist visa options.
NO, as a stay based on visa exempt entry, 30 day Extension of Stay based on tourism and conversion into a Non Immigrant Visa do not count forwards in the rules of 90 day reporting.