You've got the skills, the tools and the will. Add time and money and anything can be done. It's a question of value in the end, and whether you would rather focus your energy and resources on one project or another....
I can understand taking on a project like that and relate to it much more readily than I can understand cruisers who drift around from harbor to harbor without working or taking on new challenges. I couldn't do that for more than a year or so, unless perhaps as a commuter-cruiser with other things going on.
I don't know if you remember Symmetri, but I bought that boat in storm-damaged condition for $35k, put about $55k (and a LOT of sweat equity) into her doing a MAJOR refurb inside and out, sailed her for 3 years and sold her for $110k. I had a lot of fun, and even though much of the work was miserable/dirty/uncomfortable it was a labor of love. So to me it made sense. I only sold her because we wanted a larger boat, and Double Horizon came on the market.
I also own an old home (1858) so I do get your thinking Tom.