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Ok. So here's the situation: My Wizard (200 pounds, full gear) wants to jump inside a bag of holding (250+ pound limit, depending on bag type), have his automaton (possibly polymorphed into something with fingers like a monkey) place the bag into his handy haversack. And then Plane Shift with the 5 pound handy haversack.
20 pound side pouches: limit of a type 1 BoH.
80 pound main pouch: limit of 1750 pounds of BoH. (basically).
But what if we further nest BoH up one more step? A Type 4 BoH could hold 25 more type 4s. And that would mean the familiar could take along 37500 pounds, basically a small army (185 200 pound persons).
So what happens to the "cease to function" people in these instances. They are in a plane, inside a plane, that can't be reached until the outer plane is opened is my understanding. It's not that they cease to exist. It isn't even that they stop moving. Is there anything stating what happens to people inside such a thing? I know if something inside pokes a hole in it it wreaks the whole thing and they all spill out.
But meanwhile, the automaton can take a small army across planes for the small small price of 260,000 gp.
Now, let's say that someone wants to start a business of Plane Shifting... It's normally a level 7 spell. And can only take 8 people. So taking 184 people is like casting it 23 times.
Cost of a ticket? For normal plane shifting it would be 7th level spell casting /8. For this, it can be anything less, up to 1/23rd the cost (well, actually even less since it's a familiar doing it for free once a week).
2275 gp / 9 = ~250 gp for the normal scroll. (Spellcaster cost would be 13th level * 7th level * 10 gp * 2 castings = 1820 gp/8 = ~235 gp)
So if you sold "rides" for 25 gp once a week, with an average of 150 transported persons, that would be 3750 gp per week "profit." So paying for the bags would be a breakeven of 69.3 weeks. (Half if you craft them yourselves). So it's feasible you could start a small business doing this. And let's face it, most people can afford 25 gp to go exploring another plane as a "fun adventure." Double the rate for return trips, of course. LOL.
If nothing else as a GM I would tell you that you're not finding 150 people a week to go exploring the plains, especially if you're not a tour guide and not protecting them. You're just plane shifting them and opening up the bags to let them out.
Even if commoners can afford 25 gp for a trip, they can't afford to be away from their work for an unspecified amount of time. Also, most people couldn't manage to survive for very much time on other planes, the majority of inhabitants of the world are level 3 or less.
Ignoring the shenanigans of bags in bags, this still doesn't pan out because the market isn't there.
People would quickly learn "hey, yeah that wizard transported all 150 people to the other plane and let them out. They all died about 2 hours after they're release because they weren't prepared. We shouldn't take that trip".
Nobody complains when you sell them a finished product.
What kind of imaginary world do you live in where customers don't complain about what you've sold them?
I'm pretty sure even with your magically assembled boat customers will complain.
"Oh, it doesn't have enough ornamentation"
"The wood work doesn't look it was really given attention"
"Could you paint it purple?"
"Does it fly?"
"Why doesn't it fly?"
Not to mention you're going to have all the shipwright's for hundreds of miles angry at you as you flood the market with boats. Ruining their livelihood for years if not decades.
I wouldn't be surprised if years later the son of one of them hunts you down and kills you out of revenge for ruining their father's struggling business.
What a horrible person you are./s
Up to eight willing creatures holding hands. Do people stop being creatures when inside a bag of holding? I'd argue not.