I agree that being able to repeat the purchase is an important factor I missed. I assumed both purchases were repeatable but the OP doesn’t explicitly state this.
I also agree that, on average, you’d spend less with the first option. But I felt the advantage of the second plan in having a fixed upper limit outweighed the first plan’s advantage of having a lower average cost but no fixed upper limit. In theory, you could run out of money before winning a prize under the first option but that couldn’t happen in the second.
While it is true that there is a 25% chance of losing with each ticket, no one buys a 2nd or 3rd ticket if they’ve already won. This means that 75% of all losers will win on the next ticket.
To find the probability of winning only once, let’s take 1 - P(all losing tickets)
98% of people would save money on option A compared to option B. The 6 tickets only give an extra 0.015381 (6 tickets = 0.999756). That’s not worth an extra $150.
For fun, I assumed that all 7 billion people in the world bought tickets. After 17 tickets, there were no losers remaining. Everyone in the world should have won. (7000000000*(1-0.25^x tickets) < 1)
17 tickets costs $5800 (700+300*x tickets) which is our global maximum. Your pool should be signifacantly lower so I would expect the maximum number of tickets would be lower. If 5000 people buy tickets until they win, only 7 tickets are needed for a maximun $2800.
I just don’t see saving money as the primary goal. In either case, you’re going to end up with more money when you win the undefined big prize, so quibbling over the initial investment seems trivial. To me, the primary goal is making sure you win the prize, which is why I favored the second option (assuming it’s repeatable).
The disagreement could have less to do with mathematical proof and more to do with communication. It sounds like your compadre is viewing this game as individual trials like roulette, where the odds to not change based on number of attempts, while you see it as a zero sum game, like lottery scratch offs, where odds change in your favor based on the number of tickets bought.