I too have got a lot of vicarious pleasure (and knowledge) from the write ups of your experiences with the Commander. All the advice here, to date, has focussed on hard numbers about performance and economy. It seems to me that, for you, there are other factors to consider. For the want of a better phrase you seem to value the romance of it and since your flying has no balancing financial income it's all down to what you can afford to pay for the pleasure you get. And how to configure that expenditure to get the greatest pleasure.
You seem to get a lot of pleasure from getting to grips with the complexity of big old, elegant, planes. You seem to relish the challenges and airmanship demanded to make them do the kind of flying you want. I think you need to have a think about where your tolerance of complexity vs expense lies. Pressurisation seems to be a good example: it doesn't make much sense for you on your own, but if there is an attraction to you of owning and managing it then it becomes just another thing to put in the balance.
My only other point is about short field characteristics: unless you've got it out of your system a lot of your photos show your plane on an unmade strip in the middle of nowhere - do you want to give that up in favour of range and speed? The Aerostar looks lovely and, like the commander, ticks all the right aesthetic boxes for me (not that I'll ever afford either). Should you own one will your flying change to reflect the plane - ie do you do the dirt strips 'cos you can or is it where you want to be? Which is the tail, and which the dog?