Two kinds of theft to consider: the bike itself and your gear.
My thoughts:
1. The bike. You can almost always choose lodging that has a reasonably secure area to park a bike. It may be a courtyard, hidden area behind the building, private garage or even inside the lobby. If they don't, I'll usually go elsewhere.
I used to carry a short, stout cable lock that I would deploy if I was uneasy about the parking. I used to carry a very light weight cover that would help as well, but I find I don't carry either of these anymore. I just lock the forks.
Mostly while traveling your bike is a moving target. If someone notices that there's a nice bike outside the hotel one night, the next night when they come back to look again, it's long gone. If you stay in one place for longer periods and park outside where the bike is visible, you might want to take more safeguards.
Parking on the street during the day has never been a problem for me. I'll lock my forks if I can't see the bike or I'll be gone for a longer time.
2. Gear. This is mostly snatch and grab theft. No one is going to spend time trying to get into your gear out in public. Locked panniers are easy to defeat by someone who is familiar with them- most snatch and grab types are not knowledgeable and won't bother studying the locks to figure out how to get in.
At night, it's a different story, when they have more time to work. It's easy to keep all your gear in saddlebag liners, lift the liners out and carry all your stuff inside with you.
There have been times when I stopped at a trailhead and wanted to take a walk but left when I observed some questionable types hanging around the parking area. Sometimes I have continued on to a hotel and stashed all my stuff in my room before returning to park my bike and take my walk.
Summary: I do think about theft but I don't become obsessed over the possibility. I haven't had anything stolen in many years of moto travel.
But.....I tend to stay in the countryside and in relatively small towns. If I was going to New York or London, I might reconsider my strategy. Fortunately for me, I have little desire to go places where crime is rampant.
................shu
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