Dear brother Noah,
as you can see by the responses, there is little to no fruit gained by TRYING to feel your way to God, going outside of what is thought of as "orthodoxy".
for your question, its better, imho, to seek out brothers where you are, to hash out such questions, face to face, but on a public cyber forum, people wont really "come as are", its easy to throw flame, behind a moniker.
my personal feeling is this; from early childhood, raised in the synagogue, and then at age 42, (2002) when God was pleased to crush me, then reveal His Son Jesus to me and in me, I have never concerned myself with the threat of hell, because I have always felt something that in theological terms is called "eternal assurance".
Also, the Indwelling Holy Spirit WILL be my Helper in realizing WHEN and IF I sin, therefore being a lover of God and Messiah, I will immediately repent...turn, and out of love for God, plead the Blood of Christ, acknowledge my sin before Him, and ask forgiveness.....NOT out of "fear" of hell, but because I wish to please God, I love Him so much.
The Beauty and Grace and Mercy of Messiah Jesus is that He has FREED me from the bondage of the FEAR of physical death, Jesus has supernaturally circumcised my heart, so that I can love the impossible love, so that I can walk in humility and meekness, esteeming others above myself, TRYING to have compassion and grace to all my fellow cracked "jars of clay", who all groan while we wait adoption as sons of God.
so I rarely concern myself with hell....i'll let others "preach hell" as I've heard said. not my calling, my calling, as i'm led, is to fan into flames, this simple beautiful gift of Faith, while loving God in utter child-like dependence.
just understand, this is not the VENUE to work out, the "personal work" it seems you are striving for...and I do NOT write that in any "rebuke", I write that in the Love of Messiah.
Human beings are fond of a "carrot/stick" dichotomy, they can "understand" that....but loving God JUST for the JOY of loving God alone?....that's a tough one for some people.
and anytime you hear the words, "2000 years of Church history", my feeling is to ask, "do you REALLY want to go there?".....as those 2,000 years are so filled with the blood of innocents, so filled with the tyranny of "religious men", who had no qualms about burning people, torturing them, much like some of these "muslims" today. I see these hell hounds acting very similar to "Christians" did 1,000 years ago, who "crusaded", and all the hell THAT ENTAILED....the blood of that endeavor, across Europe into Israel cries out from the ground.
Since 315 AD, the organized "church" has largely FAILED God and Jesus Messiah..now remember I wrote "organized", as there have been moments in time, and lonely suffering saints and small groups, thru the ages who have NOT failed God and Messiah....but they have usually been OUTSIDE the "camp....outside the "temple", hunted and hectored.
God is watching...don't worry about hell,"because, if you confess with your mouth that Jesus is Lord and believe in your heart that God raised him from the dead, you will be saved." Paul as swept along by the Holy Spirit wrote that in Romans 10:9
a simple faith is best.
shortest verse in the Bible: "Jesus wept."