Hmmmm... I've owned a couple of Thorens 160s and never understood what the hubbub was about. A nice better than entry level table, but a thousand bucks? - it doesn't even have a cast subchassis and I sure hope it doesn't have the plastic subplatter... Even with the Rega (an arm which I've never gotten comfortable with, despite my very high hopes) and cartridge, I wouldn't even consider it. I'd think the VPI a much better bet, but I'd be curious what the Kenwood is selling for - it might be perfectly satisfactory.
And the System Deck (which one?) and Funk Firm, which aren't pictured - it all depends on price...
I'm not sure what you mean by 'time for me to enter deep waters', but I assume it means that you want to demonstrate your audiophile commitment (by spending lots of money). I'd caution against the notion that anything positive about your character or taste is demonstrated by spending more, and I'd caution against the notion that spending more gets you better sound. It may, but it may not, and above a fairly basic level, the cost to benefit ratio goes exponentially up, even if, in fact, you do get better sound.
To prove my point: If the VPI needs a cartridge, try the AT 3600 or its successor - you can find many iterations from eleven bucks up to closer to a hundred, but I'm not sure if there is much difference. What I am sure about is that it is a fun cartridge to listen to. Detail may be missing, but the music gets through. You could be forgiven for wondering why some people are willing to spend vastly more. If you think I'm talking through my hat, Linn made the argument that unless the turntable and arm were right, the cartridge didn't really matter that much, which is why they sold something not far from the 3600 to use with their tables.