I think you make some valid points. The ownership and running of the club has been a bit dodgy in the past. I feel that we've never had the stability of other clubs in our league and by and large we don't have the same level of history/foundation. I often question why anyone would invest in a club like Livingston. The vast majority of football clubs are are not profitable businesses. Therefore, for someone to take over a football club and invest a lot of their own money, it would take some sort of personal motive. I just don't see, with Livingston being a new club with a relatively small fanbase, there being many people who would care enough to invest money year after year. I don't exclude the idea that someone with a lot of money would want to just blow it on a football club, but it seems unrealistic that anyone would want to for more than a few years unless they really cared.
I think if Livingston can survive for a few more decades then we will prosper and find the stability that we've lacked before. We have a young fanbase at the moment and the town itself is expanding rapidly with more and more first-time buyers and families coming to live here. If we can attract/keep these young supporters then we will have a stronger fanbase and a better prospect of finding investors who support Livingston and care about the club enough to ensure it's long-term stability.
I'm not suggesting here Angelo Massone does not care about Livingston. But as you've rightly said, time will tell.