Good question and good response. I purchased two Healeys thus far. My first one, which I still miss, was destroyed from hurricane Sandy. I miss her because she was a step above a basket case, but I was advancing along, improving her and having fun driving her. Had it for two years and got it cheap by todays' standards ($23,000) and was very much complete and ran (well, more so later on)! For the two years I had her, I was fixing and detailing as I went. It was definitely a hobby and a learning process, a sense of accomplishment. Well, after Sandy claimed her, I started again. But almost paid double BUT, she was a much better specimen. It helps to have a current working knowledge of the car but still, I am treating it as a hobby by detailing and maintaining her as I go, again. In terms of whether to buy one and in what shape, I have to say it also depends how much energy you have plus money and time that goes without saying. Having a space to work in helps and accessibility to parts still okay but not as easy as it once was, even with DIY skills. The final decision will have to be weighed by how bored you are, then your available funds, then how much time you have. I live in the northeast and because of all the snow and being homebound and all, I am glad to have the Healey. Example, I am refurbishing the dash and all its related parts which I am doing in my apartment, never getting bored, never feeling any cabin fever. The plus side(s), I am also helping my investment and getting some exercise, depending on the task. Also, if you get tired of it, you can always sell it and not make it a total loss. But I still feel you are still going to have to make the final decision yourself.
Paul