Ok. So I tried again today. When I got to my favorite Starbucks my WiFi did not turn on. I opened maps and noticed that my location according to GPS was about 200ish yards from where Maps says that particular Starbucks is (note: The GPS location was correct, I recognized the building I was in). When I got home my WiFi did not turn on like it has previously. I checked Maps and noticed that my GPS location was off by over 100 yards.
So by what I can determine with this little experiment is that my second theory is what is causing the problems (mine at least).
The mapping data in Hawaii (Oahu) is not always accurate. We have weird addresses such as: 98-12345 Farrington Hwy. Both Maps and Here+ Drive won't recognize any numbers before the dash. Also, many places here share an address with different suites being what differentiates between the places.
As for the GPS inaccuracies. I can only attribute that to anomalies caused by weather, solar, and or electromagnetic interference and is probably a local problem for me and not many other people.
So my recommendation is to use the GPS location of your favorite location and NOT what Maps says is the location of your favorite.
My two cents.