Hi R.,
I'm not sure about the logistics of a project like this, but I do watch a lot of HGTV :)
A few tips i've picked up is to make sure first of all that the cabinets are wood, obviously. sometimes they're not 100% wood. I have seen them take out the center panel and replace with a frosted plexiglass because they can't stain that part... I really like that look.
Second, if you're going for the tuscan feel, you definitely need to warm them up and ditch that bleached wash.
Edit: also if you're going to stain them it is best that one person do it, because of the differences in technique and the amount of pressure you put on a brush vs. somebody else... to make sure they are uniform.
As for your comfort level with the black... I can appreciate that... I painted a whole wall with dark chocolate brown, a color wash with a caramel color and a black curve going through it all (it was an abstract print I saw online and I decided 'I can do that!' and so I did it... over the WHOLE WALL. It took time, but it was easy... and it was risky but I figured if we don't like,.. we just paint over it. But the black cabinets are REALLY in right now... it's hard to decorate/remodel a kitchen with a style that will be timeless... a lot of cabinets are now coming in a black finish... I think it spans the spectrum.... it can be casual, and it can work in a contemporary kitchen... if your appliances are stainless that can look really sharp.
And painting them can be a low cost way to update...
I say go for the black.... :)
We considered resale value when we chose the color for our granite countertops... in the end, with no plans to sell any time soon, we chose the color we wanted.
With the money you save you could get some really nice light fixtures with wrought iron to accentuate that tuscan feel :)