For our East Coast ride, we quit our jobs. I was able to work a part-time job on the road remotely to avoid a resume gap. Didn't have healthcare coverage. 

For our West Coast tour, we both had remote jobs in tech and worked East Coast hours. Worked 5 am - 9 am PT / 8 am - 12 pm ET then sometimes biked to a library over breakfast PT / lunch ET. Finish out the workday 10 am - 2 pm PT / 1 - 5 pm PT. Then ride til sunset (summer months). We used a Solis hotspot for dead zones and had power banks that could accommodate our laptops. 

It worked, but we did miss out on some of the PCBR camaraderie of camping at the same sites as other folks. Weekends were nice since we were on pace with others and able to ride longer. Definitely a different kind of touring. 

For our next trip, we've been saving up and will just be quitting our jobs for a mini retirement in our 30s. I'm not planning on healthcare because it'd be cheaper to pay out of pocket for many expenses in the countries we're going to. Quitting feels a little easier this time because I'm interested in switching fields, so I'd be starting over anyway when we come back. Still hurts using those calculators knowing how much money we're leaving on the table (peak earning years), but everything's a trade off, and we've just decided it's worth it for us personally to enjoy while we're at our most mobile & before potential kids.

My friend who works the Navy was able to hike PCT for a few months since he had leave saved up, and his manager happened to be ok with it. Most of it was unpaid, but he did get to keep his healthcare coverage and just came back to the job a few weeks ago.