@AkawntantAnne I helped my aunt complete a TV application online a year ago. She's previously working in the gov't and retired in 2017. We just indicated in the application that she's retired and attached supporting documents (i.e. pension docs/retirement docs). We also included bank statements and properties under her name.
For the question on knowing the dates of entry for each occasion, we indicated NO since we are not sure when can my aunt come back due to obligations in PH. You can say NO if you are not sure and just indicated your reason. Otherwise, if you know/have plans on returning (when requesting for a multiple entry visa), indicate the dates. As an example, when I applied for the TV of my mom (multiple entry for 12 mos) I indicated significant dates when we needed her to be in AU (i.e. attending a uncle's wedding) aside from the dates when we plan for her to stay to look after our child. Hope this helps.