When it comes to pricing I see it like this:
A new release which is a Standard Edition £40 - Anything over £40 just seems to be a con, our GAME store had Kingdom Hearts III at launch for £52.99... I had it Pre-Ordered online for £37.85... That is a colossal difference! I can't ever see myself spending £50+ for a Standard Edition release, unless it is an import at best.
Special Editions can vary, I very rarely buy them these days as most of the time they just come with tat or are overly expensive due to including a toy. I will happily pay £5 extra for a nice Steelbook - I did this recently & switched with my MediEvil Pre-order. Or I will wait for the SE to go down, I snagged Days Gone SE for £35 as opposed to the £64.99 RRP.
One thing I look out for more these days is if the game has a Season Pass. If it does I tend to try hold out until a potential Complete Edition is release - Which is really hard to judge prior to a 1 after the game has hit the market. But I'm fed up of buying incomplete games, especially if retailers are charging more for them.
I don't buy new releases Digital, I will buy games Digitally on SALE if they're not available physically (Or if they've been exploited by a company like Limited Run) - Star Ocean 4K being a prime example, I'd have bought it on disc but it was only available on PS4 via download, so I waited for it to be on sale under £10.
I'm the same with Season Pass/DLC content, I managed to breakdown Watch Dogs 2 DLC when it was on sale and bought the important Story DLC for cheaper than buying a Season Pass with cosmetic tat.