These old British cars can be fun, and yes a bit cartoonish given their size compared to modern vehicles. I have been caught with the top down once or twice. It's easier to get wet than try to put the top up.
In the big scheme of things they are cheap to build and maintain. You don't need to invest a $30,000 plus to have some fun.
You can, get a decent driver for under $8,000
There are no electronics to deal with so just basic tools are required.
You cant buy anything north american (sporty) for under $25,000
With my British car addiction and my Model airplane collection I am quite busy.