98-102 is about a 25ppg bonus on his starting price and could see him get to $500K. Another way of looking at is if Pendles goes for 115 that's only an extra 15ppg for your $300K. I reckon you could get more than 15ppg upgrading a rookie somewhere else for $300K.
It's an interesting way of looking at it, but I think you have to factor the trade into it.
Let's assume Pendlebury scores 115 every week, and plays 22 games, and Libba scores 100 every week, and most Coaches trade him out at his bye (Rnd 14). Just to make it interesting, and keep things even, let's even pretend that they trade in Pendlebury, when they trade out Libba.
Rnds 1- 12, the Pendlebury owners get a 180 point head start over the Libba owners, minus the improvement the Libba owners made with the $269,900 Loose Change. The Libba owners then use a trade and $75k to turn Libba into Pendles at Round 14.
So the equation we are looking at is, do you want:
180 points + 1 trade + $75k
or
12-13 Rounds of the improvement the $269,900 brought?
Unless the $269,900 is used to upgrade a player to a genuine Keeper, thus saving a trade. Most might assume that is does, but practice might prove otherwise. While in theory the $269,900 should bring in 50/week, in practice it is more likely to pull in 30/week. That reduces the equation to something like, do you want:
1 trade + $75k
or
180-210 points?
I think most would choose the trade + $75k.
So just like the Goldstein conundrum, I would only be starting Libba over Pendles, if I was confident the Loose Change was saving me a trade somewhere else.