Does this harness ever create an issue for male dogs in terms of being able to urinate (i.e., getting in the way)?

Not at all. We’re very happy with this harness. Been using it for years for our husky. She pulls like crazy. We’re able to control her with it:

My dog's girth is 24" but he's a medium sized dog and will likely gain weight. Is the medium adjustable down to 24"?

Lot of adjustment. Fits our 70 lb GC with room to adjust both ways

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RuffwearWeb Master, Multi-Use Support Dog Harness, Hiking and Trail Running, Service and Working, Everyday Wear, Red Sumac, Large/X-Large

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