1. Firstly, Sony is a retail electronics company and they run on a yearly product cycle. So I will bet the farm there will be an A40 series and Sony will need to add something to it that the A30 series does not have. Otherwise there is no reason to upgrade. The A20 series was the same device as the A10 except for an improved equalizer and noise cancelling. Neither of which I needed so I did not upgrade. I am only speculating about what Sony will add and bookmarking and podcast support could be two features. The lack of AptX support on the A35 is the main reason I am not 100% sold on getting the A35 as my A17 has it. So I am hoping it will be there on the A40 series. As for speculating on availability gentec is Sony Canada's chosen official online seller. When you click on the buy online option on the Sony Canada website you go to the gentec website. This tells me that gentec would likely be the first site to have an official availability date and this is the site Sony told to start taking pre-orders. You are correct the A40 series won't be available right away in Canada. But the A10 and A20 series did not get released in Canada until November and December respectively. The fact the A35 should be available much earlier this year means I may not have to wait as long for the A40 next year. If I only have to wait a couple more months after the A35 becomes available to find out about the A40 then why not wait? If the A40 does not have AptX then I have my answer and I can choose another DAP. I have my trusty A17 which was replaced new last August by Sony when I put in a battery replacement claim. So the A17 may be a 3 year old model but my replacement is only 9 months old and paired with my Q1 sounds quite good. I can afford to be patient and only buy when I find the perfect DAP for me. Also keep in mind that Black Friday and Christmas time this year could bring good deals. Especially if the A40 is announced before then.
2. As I already stated adding bookmarking and podcast support to the A35 lessens the appeal of upgrading to the next model released, presumably the A40. Sony isn't going to give features to an already released product when they can add it to the next model. Fifteen years selling audio products including Sony's tells me that much. Sony could have put noise cancelling on the A10 series but then why release the A20 series? Sony added support for LDAC to the A10 after release but the A10 already had bluetooth and they wanted the A10 series to work with their LDAC capable wireless speakers to boost sales. Sony will add a feature to an existing product if it is in their financial best interest. Adding bookmarking and or podcast support does not do that on the A35. I may be wrong but the next product release cycle starts in a few months so if Sony hasn't added bookmarking and podcast support already then don't hold your breath. Sony will be focusing on their new products to be released in the fall and if there are no more issues with the A35 you likely won't see anymore firmware updates.
3. As for waiting on other competitors, I am already waiting on the A35 so no harm in waiting for news of competitors offerings. I just found out that the Cayin N3 will be available from a store in Toronto next Tuesday. That is another DAP I am considering so now I will be able to audition it. As for buying the A35 and then selling it later you will take a financial hit each time you sell something. I am not a collector of DAP's, I buy one DAP at a time an choose the best one for my needs. It makes no sense to me having multiple DAP's as I can only listen to one at a time. Playing Russian roulette with my DAP purchases isn't something I can afford to do as I have much more important things to worry about.
When Sony chose to leave off AptX on the A35 it opened the door to me considering other manufacturers DAP's. The Cayin N3 is one, the Fiio X3-III may be another and if possible I would like the chance to audition them all and then buy the one that I like best. If the A40 looks like a better option and I am not sold on any of the other 3 then I can afford to wait until next year. God knows how many other DAP's will hit the market later this year and patience is a virtue when it comes to making the best decision.