HI Flienlow,
I will have a go at responding to your questions.
First, good for you for thinking aircraft ownership through. It is a big step and I think the type of Q's you are asking are a good start - but my advice is not to rush it. Without wanting to sound patronising, I think your Q's indicate that you are in the early stages of exploring your possible aircraft ownership options - particularly those options in the experimental and LSA categories. To be considering the Kitfox SS7, Glassair Sportsman and the likes of C182 indicates to me that you need spend some time clarifying 2 important issues: Your mission and your budget. No one aircraft will do it all.
I will make the following comments in response to your Qs in the hope of helping your decision making process:
Q1: Happy medium? I think the majority of KF owners/builders look at their investment as a long term investment in providing them with affordable, highly capable and fun and safe flying. I agree that spending $70k on a C182 would provide you with 'stable depreciation'! You will find that most Kitfox SS7 aircraft are tightly held for a good reason - they are a very capable aircraft and affordable to run. Many of us have owned and operated Cessnas, Pipers, Mooneys and Beechcraft but have chosen to leave behind that type of aircraft and the flying they provide.
Q2: Others will testify on this one.
Q3: See Q2 response.
Q4: Keep it simple and there are heaps of feature packed and cheap (relative to certified aircraft) modern panel option - this should not be a big issue for you at this stage.
Q5: Fabric covering is not hard and most people report it as being enjoyable.
Q6: Viking? Don't do it - stick to the well supported factory FWF packs. (But hen again, if you are really and experimenter....)And you have the options of some great modern engine packages - see latest Kitplanes Magazine review of available engines.
Q7: I don't know your wife and what makes her raise her eyebrows.
Q8: The great level of willing support from this site and the factory.
Q9: Wouldn't hesitate. And it would be much quicker.
Again, take your time, go and visit a few Kitfox owners, the factory, take a flight for a few hours with Stick and Rudder - this will inform you if this type of aircraft and flying is for you - if not, you get to stick with Cessnas.
Good luck and enjoy the process.
cheers
ross