If you got it cheap then perhaps it's worth considering replacing the
screen at some point. I too was a little nervous when first taking a
laptop apart but now they are just different to a desktop and pose no
real problem :-)

You cannot start a Windows install through Wine - it just won't work
so no point going any further with that one. Give Virtual Box a try
and I think you'll find it works well but it does depend on what
program you intend to run. Most work fine but anything that needs
direct access to hardware ( notably games ) will struggle and may even
not work at all so what program is it ?