I am in a high bike theft area, and always use a U lock on the bike itself (locked as in the picture above)
However, the trailer I lock with a cable, and a thin one at that:
A trailer is not worth as much as a bike, nor is it as easy to sell
A trailer is not its own built in get-away vehicle... in fact, there really is no easy way to transport it without a bike
It will take extra time for most people to even figure out how the hitch works and disattach it from your bike, and bike thieves want to work as fast as possible.
I think having a trailer attached in the first place is likely a theft deterrent.
Is the convertible feature intended to allow you to convert from trailer to jogger when the destination is reached? If so, is the front wheel always on or do I have to stow it and the handlebar somewhere? I would be so disappointed if the conversion is just meant to happen at home with tools or something.
I believe most stroller conversions can be done with no tools (or at most a bike multi-tool), in the field, but you would have to remove / attach the front wheel every time as part of the conversion.
of course if you have an old kyrptonite you can open it with a ball point pin. 90% of all locks can be defeated easily. IMHO you should either invest in a really expensive lock or one that just keeps honest people honest. Probably depends on the town you live in and the threat level.
I can pick a standard front door deadbolt lock with a $5 set of lock picks, but I spent hours trying to open a cylindrical kyrptonite lock with a pen and made zero progress. I don't doubt it was
possible but the threat was totally overblown. I upgraded to the new key style anyway, because Kryptonite did the upgrade for free. As a former bike messenger, current bike mechanic and commuting advocate, I say in no uncertain terms that kryptonite makes the strongest bike locks available - just be aware that they have multiple levels of lock at different price points. Their cheapest locks are not all that hard to defeat. There best lock comes with a $4500 guarantee for a reason. I've never heard of anyone breaking it, not even in controlled lab tests, never mind in the field.
How do you guys transport the u-locks when you don't have a trailer? It looks like it would hard to find a way to attach it to the bike without it banging around while in motion. When I'm just riding out for lunch it'd work as I could throw it in my backpack, but at the places I shop at, I can't just take a backpack as they don't want you coming in with packages/bags.
They usually come with a bracket, but if yours didn't you can get a braket at a bike shop or online, and attack it to the bike. Or bungee it onto a rack, or slide it in the slot in some racks, or possibly even hang it on your handlebar (IF it won't get in the way of steering).
When I was a messenger I used a kryptonite chain, and wore it around my waist.