Here's my two cents as a pipe smoker (almost a year now) and very occasional cigar smoker (maybe once a month).
1. No reason those can't be restored to smokable condition.
2. Check out the estate pipes from SmokingPipes.com. Also, TobaccoPipes.com sells Molina pipes. I have two and are very happy with how they smoke. They are definitely a budget pipe but they smoke well. I just purchased a Morgan Bones pipe that seems to be quite nice, though I have yet to smoke it. The price is right, though.
3. Seems like most of the tobacco you have is aromatic. I probably wouldn't hold out hope that any of it will be good. I may be wrong, though. I'd look for non-aromatic blends. Being a cigar smoker you may appreciate a good Virginia/Perique like Escudo or Peter Stokkebye Luxury Bullseye Flake. The Perique brings a nice peppery quality that is similar to cigars (at least those I've smoked). A nice English blend may also suit your tastes -- try Arango Balkan Supreme. My current go to is Macbaren HH Old Dark Fired, a Kentucky dark fired (burley) based tobacco that has some serious barbecue qualities.
4. I run pipe cleaners down the stem after every smoke (and during smokes in unfiltered pipes). I wipe out the ash when I'm done. Every few weeks I'll break out some cheap bourbon and clean the bowl and stem/shank. I have not smoked enough to really build up a significant cake in any of my pipes to warrant the purchase of a reamer. You may benefit from one to help recondition your pipes. Unfortunately I can't suggest any specifics.
5. I'm looking into buying a pipe rack to store my pipes. Right now I throw them in a drawer with the nicer ones getting thrown in a pipe sock first. I don't have any pipes that are nice enough to absolutely necessitate a rack yet.
6. My go to online tobacco shops are SmokingPipes, TobaccoPipes, 4 Noggins, Pipes and Cigars, and most recently Watch City Cigar.
7. Here's my general advice regarding cigars vs pipe tobacco. My experience is that, in general, the cigars I've had have been far bolder and a bit more one dimensional than what is available with pipe tobacco. I don't mean to disparage cigars at all with that statement, but I don't think it is a secret that pipe tobacco in general is more subtle in taste and aroma than cigars are. Keep this in mind when trying pipe tobaccos, and try to take pipe tobacco for what it is -- a more subtle experience, where half of the experience is the ritual associated with using the pipe. It's a meditative process for many, and far more laborious than lighting a cigar and letting it burn on its own for 1+ hours. The pipe requires finesse and care in preparing, packing, and keeping it lit.