This is true, a lot of short term "friends" you make along the way but a few days later each one goes their way and also it becomes a bit of a repetitive process and can be quite exhausting. It'll depend on your personality mostly but for an introspective it can get tiring. Helps if you visit friends/family from time to time.

What do people do with their homes and stuff? As a renter I don't know how I could possibly pull that off.

You do have to live with an intentionally light footprint. One thing a backpacker learns quickly is we don't really need that much stuff :)

Subletting is a good option. Most leases in major cities are year-long so you could time it around that as well.

Bottomline: most potential roadblocks are solvable.

I would put my things in storage when I went travelling, and leave the lease. Usually quite affordable, even with the big brand name storage firms.

Finding a new rental every time sounds like too much of hassle for me to have it on a schedule like that.

I found it rough almost immediately. And I'm someone who likes a lot of "me" time.

I recently did a family holiday where I had the day to myself to ski, but evenings with company. That worked well for me.

I think my ideal is the classic work at home, go on holidays model.

Is the idea here that you find a company that agrees to a start date 3-4 months in the future? That seems like a good idea that could work for larger companies. Most startups I've talked to wouldn't go for that.

Yup that's true. Another possibility is taking a bit of a risk and securing the position upon returning. I know a bunch of people who have done that without issue. This might come at the cost of some career advancement, but I'm assuming that's not a top priority for someone asking this question in the first place.

I've been doing exactly that for exactly that reason. It's worked pretty well.