In regards to hearing aid types, be aware essentially there are two basic kinds
One has inserts, mini speakers, that fit inside your ear canal, which is connected by a fine wire/tube to the larger sensor/microphone that fits around your ear. They tend to be easier to put on and remove, they also adjust to pressure changes and allow noise past the insert to your own ear. Their main disadvantage is they don't work as well when you're wearing a helmet, hat etc
The other kind are one complete piece, mike and speaker, that inserts inside the ear canal, and pretty much closes it off. They're more discrete, and work better with headgear on. They are a bit tricky to get in and out, and close off the ear pretty much completely, attenuating any noise before it reaches your own ear.
Both typically come with accessories that allow you to blue tooth to your TV, phone, and external mike.
Your audiologist will most likely be able to give you the best recommendation, but be sure to fill them in on your job requirements, hobbies, etc.
The CAF support, in resupply, can vary depending on where you are. Expect to go through batteries like crazy, and there are also small accouterments that fit on the hearing aids that'll need replacing from time to time. Be sure to find out with the health unit you're dealing with how that support will be provided (who is paying?); this can be an issue if you're doing a Class B some distance away from any health care unit.
Start a claim immediately with VAC for this, be sure to be as complete as possible in describing what you're contending with. The response time can vary considerably; some get a positive result in a few months, some can take years. In my own case it took ~12 years to prove my hearing loss was service related, despite being in the artillery for over three decades. In the end, it's worth it, because once you get out your support for hearing aids ends, and don't expect your provincial health care to necessarily help you (I don't know any that would cover the cost), so it will come down to just you and VAC.