djb

Afro feller, interesting idea, but what I can add is that from my experience living and travelling in Latin America, not only are you dealing with simply being on a bike tour, which takes mental and physical energy (ie not a hell of a lot of oomph left at the end of the day) which would apply to travelling by bike in Ontario, Canada or Florida U, S and A, but you'd be dealing with a lot of other factors being in far off countries.

I'm referring to the regular stuff, dealing with change of cultures, figuring out slowly when to be wary, when to not worry, figuring out language and communication, be verrrrrrrry wary of security overall, keeping track of your stuff (even moreso when on your own).
I've travelled on my own in Central America, but even back then I had the advantage of being somewhat familiar with "stuff" and had a reasonable take on the language.
I've also biked in the area, but both times with a riding partner, which made things easier security wise.

On my bike trips in the last few years, I can say that it takes a lot of energy to write after biking in the day. And yes, you can hold up in places for X days and work, so of course things are doable, but given that you havent bike toured before, its easy to imagine you "working and travelling" at the same time.
re security, you'd have to be very careful of thinking out the nuts and bolts of stuff also, ie keeping a device working and safe, keeping work backed up and safe, what if worst case scenario happens and some dude stops and sticks a gun in your face and steals everything? Is your work backed up, will spotty or non existent wifi allow you to backup stuff properly? Not fun scenarios but necessary crap to think about if you're responsible.

heck, and then we get to the whole covid thing. Developing countries are going to be down on the low rung for vaccines, and this may even exacerbate the whole "rich gringo" thing that as rich gringos that we are frankly, we have to be aware of being there in how we are seen and perceived, so if its "rich effing gringo who also has had a vaccine while I've / we've been suffering here and even poorer than before"----you get my drift.

just throwing out ideas here, don't want to rain on your parade, but there's a certain amount of truth in my views.
In reading over what I wrote, I think the covid thing may be the biggest obstacle. The mierda going on in both of our countries (I assume you are a Yanqui) aint over, and the fat lady wont be singing for a while , and being fat and with high blood pressure and all, I hope she can still sing if she gets covid going to the local Walmart.....

you know, if you're at all serious of this idea, I highly recommend that you start working on acquiring some Spanish. It's a slow process, that's normal, and worth it if you have more time and can stick at it gradually. Getting even the basic use of another language always has pluses in life anyway, so there's no real downside to starting now, even if you decide to go to Albania or Singapore to work and travel.
cheers
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ps, from your previous touring experience, which I didnt really register to be honest, you've got lots of experience being in other cultures, so you're very aware of all of this side of things. Sorry I didn't catch that properly.

I can only give rough estimates of daily expenses for some Central American countries and Mexico, but it would be very easy for you to check out recentish Crazy Guy on a Bike South American journals to get good cost estimates for various countries. Check out Tim Towers stuff, he's an older guy who has biked a lot in Central and South America and is a prolific note taker, great for details and costs etc.
At least with cgoab you'll get a good idea of costs from the last few years, which should be relevant still.