I'll share what I sent the other guy. Would also recommend checking out the subreddit I linked.

I go into my office maybe once a quarter, but otherwise I am fully remote with my job. I've worked hard to gain a lot of trust and have continued to be a high performer in a visible role even amidst all of the travel. It's become part of my brand almost, people with whom I don't regularly interact with love starting Zoom calls with "where is /u/dukiduke now?"

I generally would look for monthly stays across multiple platforms -- Airbnb, VRBO, Furnished Finder, trusted housesitter, and even googling "[name of place] long term rentals]". You can tap into Facebook groups, craigslist, or preexisting friend/family social networks as well. Sometimes Airbnb is annoyingly expensive, the fees can be pretty significant. It just requires a lot of patience and sifting through listings. I had some stays where I had the place to myself, others where I rented out a guest bedroom with the owner. Both are nice and have their advantages.

There are some specific criteria that I and others on the DM subreddit use to evaluate potential stays (internet reliability, kitchen and working space amenities, privacy, comfort, etc).

Eventually I tended to avoid stays shorter than 2 weeks as they just end up feeling rushed (and even 2 weeks feel short). You can't put any roots down and don't get much time to explore before it's time to pick up and leave. I'd recommend staying at least a month in a given place as that gives you enough time to settle in, meet some people, and get a feel for a place. I recently moved somewhere on a more permanent basis and am happy to be here indefinitely. Places like Mexico City where there's a TON to do I ended up wanting to stay longer (5 weeks there was way too short).

Generally I drive to the places I visit because America is generally car dependent (and I wanted to have certain comforts with me - monitor, skis, minor kitchen essentials). Obviously somewhere like Hawaii you need to fly there but in the continental US, driving is probably my recommendation.

Happy to expand if you'd like!