What I have previously noticed about StreetView in Google Maps - Probably not relevant to your question on GoogleEarth Drew - is that if it wasn't available, to look for the nearest business, shop or whatever, near to the area where I wanted to search.
I clicked on that business and somewhere in the description or photos, it had the small map view with the StreetView icon, which I then could click on to get StreetView access on the map and I could then follow along the Street for a while.
Often, the access on StreetView ran out and I'd have to look for the next nearest business. This made me think I'd found a secret way of accessing it! 😆
I tried to do the same just now via Safari and had no trouble getting StreetView access in GoogleMaps at all, so whether I had just stumbled on something strange at the time, I'm not sure.
(I also just tried getting into GoogleEarth on my Mac via Safari and was told my browser didn't support it)
I think Google is progressively introducing a new way of "moving" in Streetview: the arrows ('>') seem gradually to be being replaced by blue lines. Nasty things seem to happen where one scheme ends and the other starts.
At the weekend, I was looking at a shopping street and thinking it seemed out of date, my other half clicked in a slightly different position and got up-to-date imagery (mine was probably 6 years old!). Both of us were using nominally identical set-ups on iPads.
As a constant user of "Earth" I have noticed lots of changes over the past years, e.g. if you zoom into Bournemouth as far as you can, then using the arrow heads under the "N" on the top left of your screen you have a clear panoramic view without using Street Level. This facility in and around Dorchester isn't available.
Whilst using street level, looking at where I used to live in Bucks, travelling from west to east towards the house is an old version, if I travel from east to west it changes to a new version. Our house one way is as we used to have it, the other way has a new side extension.