In response to DevBGDev, I was really excited to see a new version come out so I downloaded the update on all my devices. It looks like it was more of a security update than anything framework related.
I have been working on this issue and have spoken with several senior advisors to no avail. This is a huge pain for me since I use bluetooth so much.
I have a few theories on what could be causing it, but one definite thing I was able to find in the analytic logs was a message stating "Firmware crash detected" related to bluetooth, and it clearly states that 2 devices were connected... then a crash occurred and then 1 device was connected (my apple watch, which has had no issues connecting).
I am on iPhone 11 Pro, 14.4.1. This issue seemed to start occurring on 14.4.0 for me, although I dont remember when I downloaded that version... its been a few weeks now.
I have done every troubleshooting step that has been provided.
I noticed a few things when I went down the firmware crash troubleshooting, I found out my SEID was "0000000...." Thought I had a chance fixing it with that but I reset network settings and populated an SEID... didnt work.
Next I was wondering if theres some modem firmware that I am missing, possibly old or outdated. Also, I think there's a possibility that some interaction between my apple watch series 3 and my iphone is causing a failure/bug. I notice the airplay icon will connect the first time, then as soon as I play music it will disconnect. Then after that the airplay icon just glows as if its trying to connect. I'll force a connect and it will just fail again.
I will be speaking with a developer tomorrow to hopefully try and track down this issue, it may not be of high importance in terms of impact, but it really is annoying for the time being.