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It sounds as if you are battling with a lot of emotions about this. Quite understandably. What ARTelevision says, I agree with, but really I think the best thing to do is to really look and see what's around, and if there is a niche for the work.
Personally I'd avoid the Chicago offer like the plague as there's absolutely no need to move anywhere, and I can't figure out what he can actaully offer. If it's so good for him, maybe he can offer an advance payment?
I think you are offering your wife very pragmatic and loving support. There is nothing rarified about the general art market, and if you have doubts about making a living from the work yourself, they are probably justified. As you say though, it's difficult to make judgements, and not very wise either. Just because it doesn't suit one person's taste, it doesn't mean it won't suit a whole load of others. I'm often amazed at what people buy - my work included!
I think honesty is as elusive in art as it is in anything else in life though - and honesty in people, when it comes to practical application of opinions, is a rare thing too. However, if the artist is honest, it means the work is coming from a deeper place, and that resonates with others.
You sound honest, and caring. Just keep doing what you're doing, and looking and learning and staying open to possibilities that maybe seem unlikely, and be careful to only act what you are comfortable inside.
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