@Space Puppy I haven't made it around to testing two boards in parallel, like I said I've been too busy for this. As for the theory behind it, I think it could be done safely but you are limited to one Red Board for every 2s1p set. So in your case you'd have two separate 2s1p batteries that you'd run with one Red Board per set. Then run these two Red Boards in parallel to the portable. The way the Red Board isolates a battery from load while charging makes me believe it can isolate parallel batteries from each other to while charging. I would NOT use this theory in a series set up because protection boards are dangerous to use in series.
Not possible, the smart chargers would confuse each other's CC/CV cycles.
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Look, I understand you want to build the most functional portable possible but here's the simple truth with battery powered electronics. You are in the presence of electricity almost 90% of the time in your day to day. And anywhere you'd want to SIT down to play a portable you'll have access to a charging source. The only place I can think of that you wouldn't have access to power is if you take public transit or are at school/college. If you are taking public transportation your commute will be short enough you can go 30 minutes without playing if your battery dies. And at a college, you can go to the library and plug in. The only time I'm personally not in the presence of electricity is when I'm dirt biking or skiing. As you can imagine when I'm doing either of those activities I'm not really interested in playing my N64.
As for the other 10% of the time that you are away from electricity, you have plenty of time to get a full charge for those situations. I mean you have to sleep at some point during the day. And if you like 8 hours of sleep then that's plenty of time to charge a portable.
Here's a quote of what I generally tell people: