Comparing the theology of Paul and Hebrews

[DISRAELI]

And that would be very typical of Paul in his early ministry, not being spiritually alive, coming from a pharisaical background, legalism and all.  Would indicate Paul wrote to the Hebrews early on in his ministry?
I guess 
I always liked how Paul’s messages connected so clearly with the Sermon on the Mount

"Early ministry" doesn't work, because there are various indicators of a late date for Hebrews. The whole theme of the letter (e.g. ch10 vv32-36) makes it apparent that the intended readers are converted Jews who have been Christians for a long time, and are showing signs of gtting tired of waiting for Jesus to return and being nearly ready to lapse back into trusting in the law alone. Hence the earnest appeal of ch6. There is a hint in ch3 that they resemble wilderness Israel in that they have been trying God's patience for forty years and are in danger of missing out because they are not standing firm.

All the signs are that the intended destination is the church in Jerusalem. I can't see Paul talking to James in these semi-authoritarian terms, but a disciple of Paul (Barnabas has been suggested) might talk in this way to the disciples of James.