In my own work, helping people with money stuff has straddled remedial and compensatory learning.
Remedial learning is about learning the information or skills a basic education is supposed to provide in any given context. For example, in most industrial nations, people are expected to learn, in school, how money works. I'm not talking high finance here: I mean the simple stuff like how many fives make a hundred, or how much change to expect when you hand over a ten for a $5.69 purchase.
This can be done with pen and paper, through roll playing (with or without props), or using computer programs like the Loose Change game pictured below.
Remedial learning can be functional. Presumably, it should be functional, but I'm not always sure that's the case. It becomes more functional, I think, when it crosses modalities, if I can put it like that.
Sometimes, when people play loose change, they do better than they would just working things out on paper. In that case, I usually encourage some paper work just to fill out their understanding. Sometimes, people bring pencil and paper to the game, which is fine. I do remind them that they're unlikely to have paper the next time they're at the cash register. But that's okay. Sometimes, people say things like, "I can do this easily when I have real money in my hands." That's a good thing, but it doesn't mean they can't benefit from approaching the problem in a different way. (Assuming, always, learners are choosing these tasks on their own.)
Another example of remedial learning is helping learners fill out cheques. I usually make up some bills - just numbers, nothing fancy - and then get them to "write cheques" using these (doc, pdf) fakes. [Update: these links aren't working, and I don't know why - sorry.] Again, this is something we assume people learn in school - though my parents taught me, and I'm sure I never received any such instruction in my twelve years!
There are lots of money related remedial tools out there on the web; including some pretty fancy ones like the Understanding Your Pay Stub lesson that's part of Issue 6 of the Wellington County (Ont.) Learning Centre's Learning Edge online tool. If you're not sure where to start, I'd suggest going on NALD and searching for money in the Learning Materials section of their Library.
Compensatory learning is about tasks, not skills. The goal is to find ways learners can compensate for an absence of skills or information.
For example, one time I and my lower-level learners used blank business cards to create our own wallet-sized guides - cheat-sheets, if you must - that showed what the after-tax cost of certain purchases would be. Lines on the cards read, "$10 plus 15% tax = $11.50" and "$15 plus 15% = $17.25" and so on. These were compensatory tools.
Another time, a gentleman and I wandered around a grocery store with a calculator. He was learning how to do his own shopping - how to feel secure that he had enough money to cover the items he brought to the cash. We'd spent some time earlier just using the calculator to add, subtract, multiply and divide. We spent some time totaling his bills, and playing with different payment plans. Then we did the store trip. From that point on, and for the first time in his life, he was able to shop independent of others.
Compensatory learning is always limited and always powerful - a vexing combination for everyone.
I understand the view of remedialists that calculators should be kept from adults unable to add or subtract by hand. But that's about schooling and, not incidentally, about telling people what to do. I worry less about remedial learning than doing what I can to make people's lives a little better right now, today, tomorrow at the latest.
Which is, I think, the work of literacy.