You can apply for a Single Entry Tourist Visa which gives you 60 days of stay, than go to Malaysia as planned, come back into Thailand without a visa and get 30 days Visa Exempt Entry, which can be extended once with another 30 days.
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.