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Find an Audio Shop that has demo digital that you may borrow and take the equipment home and play with it in your system.OrPurchase used gear from Audiogon. If you're unhappy with the performance of a piece put it back up for sale.
The OP's question asks - will ~$500 DACs provide a reasonable sound improvement over what I have? - or do I have to spend $1000+? - or should I get an inexpensive DAC now and wait for technology? I'm not sure "get a modified Squeezebox, a USB external drive, another external drive for backup and an inexpensive laptop for remote control" helps him out. I cycled through two mid-priced DACs - The MHDT Paradisea (stock except for WE396 tube upgrade) and the Stello DA100 Signature (stock). Neither provided enough of an improvement over the internal DAC in my Rotel RSX-1056 receiver to warrant keeping them. They were both bought used off of Audiogon, so I had to "buy it to try it". Although I kept each of them for months, It didn't take more than a week to A/B and get very familiar with their sound compared to my original setup. And I did get back 90%+ of my investment. I agree that each passing year gets us a little closer to smoother and more musical sound from a DAC. My next possible step might be one of these new DACs: the Eastern Electric Minimax Tube DAC or the Audio by Van Alstine Vision DAC. The user evaluations and comparisons are just starting to come in on these. Being brand new, there won't be any on the used market for awhile, so for now the price of admission is $800 - $1100. Steve