Chronic Venous Insufficiency (CVI) with Possible Superimposed Cellulitis or Deep Vein Thrombosis (DVT): The patient's symptoms of worsening numbness, difficulty walking, and the fact that he is already using treatments for venous insufficiency (cream, stockings, elevating legs) suggest a progression or complication of CVI. The numbness extending to the calves could indicate a neurological component or severe venous congestion.

Peripheral Artery Disease (PAD): The worsening symptoms in the legs, including difficulty walking, could be indicative of PAD, especially if the patient has risk factors such as smoking, diabetes, or hypertension.
Diabetic Neuropathy: If the patient is diabetic, the numbness extending up to the calves could be due to diabetic neuropathy, which affects nerve function.
Chronic Peripheral Neuropathy: Causes other than diabetes, such as vitamin deficiencies, alcohol abuse, or certain medications, could be contributing to the patient's neuropathic symptoms.

Deep Vein Thrombosis (DVT): Although the patient is using stockings, which are preventive for DVT, the sudden worsening of symptoms could indicate a DVT, which is a medical emergency.
Cellulitis or Other Infections: The worsening condition could be due to an infection, which needs prompt antibiotic treatment.
Acute Limb Ischemia: A sudden decrease in limb perfusion could cause severe pain, pallor, pulselessness, poikilothermia, paresthesias, and paralysis, which is a surgical emergency.

Guillain-Barré Syndrome: An autoimmune disorder that could cause rapid onset of muscle weakness and numbness, but it typically presents with ascending paralysis.
Vasculitis: Inflammation of the blood vessels could cause a variety of symptoms including skin lesions, numbness, and weakness, but it is less common.
Lymphedema: While the patient is using treatments that could be related to lymphedema management, the acute worsening and specific symptoms of numbness might not fully align with typical lymphedema presentations.