I have not done it.
What I have done in 2016 was
- quit my job
- empty my townhouse, put everything in storage and get a management company to rent it out
- go touring for 18 months (Alaska to Argentina)
Also in my dreams is essentially selling my townhouse, going touring for a few years and settling elsewhere after that. I have met people during my travels who have done what you suggest. A few general logistics comments...
1. Some things have become easier in the past years. In particular, I have use a few services, even now (a) a maildrop company. Any mail that gets sent there causes a notification to be sent. Upon that notification, I can have the mail scanned (b) an IP phone. One useful aspect of this phone is any messages left are recorded to mp3 files and sent to me by email. By selling a house and gettingrid of stuff, you can get rid of most need for many calls/mail. However, maildrops and IP voicemail still help in those rare cases, e.g. when cycling in Bolivia one of my investment accounts sent a message I needed to respond.
2. Health care and insurance become their own area to address. There are alternatives here, but useful to think through. Some of this will also depend how much of your time you spend in US vs. other places.
3. My trip was always defined as temporary in nature, so needed to think through "re-entry". In my particular case I had been over-optimistic on how quickly I would find my next job. I found one I enjoy but it took a bit. This has influenced my dreams of my next open-ended journey. Essentially, assume it will also take longer or even use it as excuse to more permanently "retire".
4. I don't have kids, so no particular perspectives there. One pointer I will provide is Nancy Sathre-Vogel (they used to have a site on familyonbikes.org but doesn't seem to be up at present - here is an archived copy -
https://web.archive.org/web/20180807...lyonbikes.org/). It wasn't open-ended but they took a 2.5+ year trip with two 10 year olds from Alaska to Argentina. Nancy would likely be good person to provide pointers to other families in similar setups.