I just thought of a few more things.
Get her to check the toilet carefully and ensure she is happy. We females have different needs to you blokes.
A good loo can be the difference to having a woman on your boat twice or not.
A normal marine toilet without a holding tank is illegal. You are not allowed to put raw sewage into enclosed waters like Sydney Harbour. Also going for a swim just after someone has pumped loo paper and other floaties is complete turn off. I have a porta potty.
How easy is it to get back on board after a swim?
How long is the boarding ladder? It needs to go a long way down in the water if you do not have big muscles in your arms.
Is there a transom boarding / diving platform. (These can be retrofitted and makes life much easier)
How easy is it to get on board from a dingy or a wharf? Things can be done to make this much easier.
Are the safety lines and posts solid and can they be easily undone to transfer people / esky and bags.
If they are wobbly it is a difficult job to make them more solid.
Basically get her approval or if at the moment you do not have a significant other female and want one to come sailing in the future... get a female opinion.
Diana