Turning up like a bad penny
is a saying, which people often use jocularly about themselves.  Presumably a bad penny didn’t operate the locks in a public toilet!

To have the wherewithal
means to be able to afford something.

Shopping around
can take a long time.  It involves going from shop to shop to see where the best value for money is to be had.

A shopping spree
is an outing resulting in a lot of purchases.

Making a splash
usually involves spending a lot of money.

Going the whole hog
 is the opposite of doing things by halves.

To have a stake in something
has nothing to do with vampires, but more to do with betting.  A shareholder has a stake in a company.

reminds me of the folk song The Wraggle-Taggle Gypsies-O, which tells the story of a well-to-do young lady who ran away from her comfortable life.  It means cushioned from hardship.

He’s raking it in
like a croupier.

A penny farthing
was a bicycle with one wheel bigger than the other in a similar ratio to the two coins.

A penny-farthing photographed in the Škoda Auto Museum in the Czech Republic

(Wikipedia commons) http://en.wikipedia.org/wiki/File:Ordinary_bicycle01.jpg

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Another penny farthing.Penny farthing
is an expression for meanness.

Last of the big spenders
is often used ironically to describe someone who doesn’t spend much.

Down at heel and on the breadline
are idioms about poor people, who cannot afford new shoes or even repairs and are struggling to buy enough food.

Cutting your losses
implies taking a decision which will prevent you from wasting more time or resources than you already have.

Don’t throw good money after bad.
This is advice about not continuing to spend on a project or cause, which is not succeeding.  Money is neither good nor bad.  It is how it is used that is important.

She’s worth her weight in gold.
What a lovely compliment!

He’d have the shirt off your back
refers to someone who charges a high price.

Jesus used the same imagery in his teaching on revenge in Matthew’s Gospel Chapter 5 verse 40 “And if someone wants to sue you and take your tunic, let him have your cloak as well.”