I am not really sure what path I am on, as it got really murky beyond stream entry for me.

As far as your question:

As far as my experience goes, dealing with thoughts becomes even harder and requires more skill after stream entry. From my current vantage point, my 1st path dark night seems like a carefree walk in the park, although that was probably not my experience at the time.

To me the whole idea that stream entry as it is defined here clears up self view or any other fetter "once and for all" is somewhat misleading. Of course, what I consider fruitions may not actually be fruitions so this must be taken with a grain of salt. I would say I have the capacity to see things as non self if I am with my meditation object, but that is not always the case as of yet in my experience.

The general trend for me has been to have thoughts be more like other phenomena-- just arising, functioning and departing. The more the habit of regarding thoughts and feelings as constituting an entity within the body looking out through the senses has been released, the more thoughts and feelings arise with some degree of clarity.

Yes there have been periods during which this relaxation of identification with thoughts and feelings has released repressed material, causing surface destabilization; but over time this alternation of surface calm and surface destabilization has trended towards more deep-level existential coherence of some kind, making authentic inter-personal presence arise more naturally. A huge part of this is seeing thoughts as thoughts, emotions as emotions, and perceptions as perceptions, and seeing these things in real time. Oh, but remember that thoughts/feelings exist on a spectrum of subtlety from coarse to very subtle. An example of the latter very subtle thought/feeling would be a transpersonal identity such as the witness, which is a very subtle thought being mis-perceived as self. Sometime soon after stream entry I fell into a pretty strong transpersonal identification, which at first I interpreted as merely having more 'presence' in the face of coarse thoughts and feelings. The takeaway lesson from seeing through that experience was that we don't need to 'disembed' from any level of mind function (into a subtler one) in order to awaken; all that is needed is letting go of the reference points by which we attempt to solidify experience into a concrete subjective experiencer in relation to a substantial experience. Disembedding results in a change in subjectivity, the potential value of which is simply to challenge subjectivity (the sense of being a subject having experiences) in general not to switch one form of subjectivity for another subtler one. The danger of a disembedding approach of shifting identity from coarse to subtle is getting stuck in a subtle identity.