I think anything like that you put on him is likely to be damaged or snagged in the chain link.
Why not take him for some short trial runs, pop in randomly to see how he is doing and gauge your experience that way? Personally, I would opt for the petsitter.
NAPWDA Certified Cadaver Dog
Waiting at the Bridge (italics
=GSDs) (hemangiosarcoma=blue):Grim , Cyra, Toby
, Rainbow, Linus, Oscar
, Arlo & Waggles