Monitoring (acoustics are part of that) first and foremost! And never pull out a loan...

Once the playback side is really taken care of, you will also much better be able to judge what hardware outboard is doing for your end results. I feel that a high end compressor cannot be surpassed by emulation when it comes to plasticity, depth and groove, so after monitoring that is where I would look first.

(For monitoring I went with calibrated Dutch & Dutch 8c's. Never had to look back since I bought them in 2018.)