I almost stopped reading at 1mg of a'dex per week for 240mg of test/week, assuming you are injecting 200mg/ml test. However, I kept reading and your current weight is 200 lbs. and you want to be at 185 by the end of January.
I think your TRT protocol needs a little improvement, despite it being scripted at that level.
At the activity level you are currently engaged in and only taking in 1500 calories/ day, you should be well under 185 lbs. by the end of January. You actually may need to increase your calories; it sounds like your body has hit a wall.
Play with your diet a tad and lower that anastrozole would be my suggestion until you get dialed in at "normal" reference values for free T and E2.
How extensive is the labwork your Dr. is pulling? Are your thyroid values in range, because something isn't quite adding up.
On the HCG, most guys find 250iu 2x/week to be sufficient. After you get your TRT squared away, you may find that you have reached you goal and recomped your body a great deal.
Of course, after your TRT is nailed down, blast away if you desire, but since you are on TRT, there's no need for a PCT and no need to taper your dosages.

Be aware that most prop is 100mg/ml so you are really going to be injecting large volumes of oil. Personally, I would inject prop every other day and stagger it around my scripted TRT.
Edit: No need to cut out red meat, IMHO. It's extremely easy to eat "clean" and consume red meat. Fats are a necessary part of your macros, so throw some fish in a couple of times/week, even though your are consuming avacado. If it's in your budget, grill some steelhead with the skin on. It's one of my favorites!!!