Went ahead and did it. Ran the tool, went through its' recommendations, and picked a few that looked decent. Shipped ~5b of stuff from amarr to jita using a pushx rush contract.
The items were as follows: 70x silo, 10x prowler, 2x pithum a-type invulnerability field.
The a-type invulns sold exactly as expected, making me 156m.
Silos were selling for 18m in jita compared to 6 in amarr, presumably because of patch speculation. I sold 23 before prices crashed, sold many of them for a small profit, and also sold a dozen or so for sort of an intermediate number.
I sold 3 prowlers for a profit of 50m each, and then the price crashed to about buy price plus 10m. There are still 5 left on the market that I haven't spent enough time 0.01ing to sell, but I've decided to pretend I sold them at their present price and see how much I made.
The answer - after tax and so forth - seems to be that I made a profit of about 750m. This is not bad for the amount of work involved.
My takeaway is that in the case of the prowlers and silos, I bought too many -- silos were about 1/3 of jita's daily movement, while prowlers were about 1/2. In both cases they crashed to much lower profit margins before I could sell more than a fraction of my stock. In the future I should use more like 1/6th of the buying system's daily movement. The a-types which sold properly were 1/10th.
Also, when there's a profit to be made, expect to spend time 0.01ing, because everybody else is going to want in on the action too. Also, things that are dramatically out of line with historical values will probably tend to correct quickly. Unless there's an actual reason for it.
In terms of doing this more than once... yeah, probably. It would have to be my primary profession, if I was going to spend time 0.01ing. I might decide to take a month, do nothing but trade, and see how it goes.