> they got to do something kind for someone

And he never needs/wants this benefit of giving for himself? Because he never describes paying it forward, in fact quite the opposite.

And again, he repeated describes never failing to get the help he seeks. Either he is taking advantage of people, or he is the luckiest person on the planet.

Interestingly, I have some similar incidents in my past: I took the Amtrak to Crescent City, then bicycled south along the coast of California. On the train up I met someone from Eureka, who invited me to stay at their place when I got there the second night, and I did. It's been so long I had forgotten the situation until just now, and I don't remember the conversation leading up to that. I don't think I was pushing for a place to stay; I stayed at a hostel in Crescent City the night before, and another somewhere near Leggett the night after, and I never slept indoors for free on the rest of the trip.

Later, when I was looking for a public trash can in a small town, I asked someone if there were any. They said no, and just to toss whatever I wanted to get rid of into the back of their pickup, and they'd drop it at the dump the next time they went.

My knees got extremely painful by the time I reached San Francisco. At a hostel near Muir Beach(?) I ran into a guy from San Diego (where I lived) who took half my gear (lightening the load) and gave me a Mueller knee brace he happened to have with him to wear for the rest of the trip. That act definitely saved my trip.

Still later on the trip, camping at a park I ran into a guy who was also bicycling, homeless by choice -- he said he was divorced and living without an address to deny his ex her alimony. He said to never go into a grocery store without checking the dumpster out back first, and handed me an over-date yogurt :-)

But I can very confidently state that I wasn't asking for any favors. Maybe that makes me not "open" to the world looking to help me?

At first I questioned whether I was being judgmental. But writing it out as I did convinced me I was not. If people are helping him at every turn, even people far less well off than he is, that is clearly him pressing the world's "kindness" button -- hard.

"We ended up sleeping like sardines under a single home-woven blanket while snow fell." -- how would he have kept warm if they didn't share the blanket with him? Did they have any option but to share their blanket or feel like they were leaving an innocent to freeze?

Actually, I have an experience for that as well. When I was prepping for the California ride I rode through the Cuyamaca mountains east of San Diego. I brought no clothing but a bike jersey and shorts. It dropped well below freezing that night. I spent the entire night huddled in a bad K-Mart sleeping bag, dozing, shivering, and cursing how long it was until dawn. I suppose I could have knocked on any van or RV at the site, but I didn't even think to, even though I was legitimately freezing. Again, maybe I'm not "open" enough, but I made a stupid decision to not bring better gear, or at least a jacket -- I earned that consequence, and I paid for it in full. :-)

And I tell that story all the time. At this point I don't think it's a better or worse story/memory than the one I would have if I had asked someone for help and received it.

I've received help many times in my life. But again, it rubs me the wrong way if someone purposefully and repeatedly throws themself into deep water, expecting others to rescue them. And to me at least, it seems clear that's what he's done.