I hope you understand that I'm not discounting your suggestions. I will definatley bring all this to the attention of the dermatologist.

Here are the values for the Iron and Celiac's I've mentioned:

MPA Serum IgG - 978 (717-1411 mg/dL)
MPA Serum IgA - 108 (78-391 mg/dL)
MPA Serum IgM - 110 (53-334 mg/dL)
MPA Serum Kappa - 786 (534-1267 mg/dL)
MPA Serum Lambda - 464 (253-653 mg/dL)
MPA Kappa/Lambda Ratio - 1.69 (1-3)

The brownish spots on my torso only inflame when I scratch, and yes, the redness is from scratching myself raw - those are spots of blood. I have noticed a pattern of itchiness first, and the scratching brings the "rash", which I am fully aware can happen without the disorder but might be Darier's sign. Hot showers will net the same result. The itch will last anywhere from 1-4 days, after which I'm exhausted. edit: None of my lesions are blister like. They appear hive like.
The hyperpigmentation on my back has been there since I was @12-13yrs old and I don't know if its related to all this or not. It's just in my photo collection for reference.
I try to not take the Benadryl often, and when I do, the lowest dose, and mostly at bedtime, but as I mentioned, if I'm not itching, I won't take it. The most I've taken is 4 days in a row, with a pause of at least 2 days.

I realize this is all speculation and only a doctor can confirm or rule it out.
I will start a food/symptom journal, thanks for that advice!