Clearance under that headtube will be a problem going down gutters (going up is OK). I don't normally go up/down gutters when towing a trailer, but I can see how it could be a problem. the more I look at it, the less I like that headtube bearing hanging down there waiting to get bashed into something.
I don't want to do any modifications just yet because I'm going to put a Schwalbe Stelvio high pressure road tire on it and get out for a 4-day long weekend camping trip with a few buddies, in a few weeks. I'll probably carry about 40lb of gear and do maybe 200 miles on the bike through a whole bunch of different terrain. When I get back I'll have a clear idea of what needs to be modified..... and I'll put some paint on it after that

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Should I put this build into the "Trailer design tips" sticky thread?... or maybe a moderator can merge this thread into that one if you guys think it's worth keeping for future reference?