Hello
I tried to fill in your sheet, but I only am familiar with a couple of the pedals there.
But maybe this will help:
I had and used and loved my Roland RC20XL looper - I still have it - but I just bought it's modern equivalent, the Roland Boss RC-30 to replace it in a new pedal set up I am building. So far (after just a few days use) I am liking the RC-30 just fine - it has several advantages over the 20XL - like some nice effects including a sort of 1/2 speed drop sound, and so on - the ONLY thing I am really missing, is the REVERSE function - it's gone, and so is the jack for it - so no more reverse. But - I can just add reverse into any loop by putting reverse delay into the rest of that patch - so it's not a deal breaker - but I DO miss it - it was really nice to have a FOOTSWITCHABLE reverse button - i used it ALL the time.
A note about the RC-30 - if you have an FS-6 footswitch - it will actually perform FOUR functions for you - which is amazing given that it only has TWO switches:
1) LEFT button - LONG PRESS - de increment preset down by one
2) LEFT button - SHORT PRESS - switch chosen effect OFF or ON
3) RIGHT button - LONG PRESS - up increment preset by one
4) RIGHT button - short press - switch between LOOP1 and LOOP2
That's good value and it gives you total flexibility in a pretty small package - one RC-30 + one FS-6 footswitch.
IF you don't care about COMPACT - then just get an RC-300 - it's all built right into that one - and it has THREE loops plus effects - but, it's BIG. I used it extensively and have no complaints - maybe the ULTIMATE in Roland loopers - worth having, I think.
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Next - your DD-6
I never owned the 6, I think I stopped at 2 or 3 but I am not sure (I think I still have a 3) - I stopped buying single stomp delays quite some years ago - because larger delay stomps can give you so much more functionality.
I like the old Digitech Time Bender - it's an awesome stomp delay - but there are SO many brilliant delay pedals out there...
In a modern version - the Earthquaker Avalanche Run Reverb / Delay is pretty awesome especially if you get the expression pedal
Two VERY different delay "experiences" there (Time Bender vs Avalanche Run).
However - I am using exactly NONE of those delay pedals in my live set up now - I am relying on preset delays in one of two more complex devices - the HELIX LT or the EVENTIDE H9 - I have one of each, and the Digital Delay sounds I can get out of those two boxes is really all you will ever want for live.
My entire new pedalboard will be three things only:
1) A very extensively programmed
Helix LT with hundreds of rhythm and SOLO level presets pre-created and saved - with the ability to load the "best" 127 sounds in in seconds
2) An
Eventide H9 inserted into the Helix's effects loop, with 99 of my hand-selected very, very favourite and good sounding algorithms - and controlled BY the Helix's external MIDI functions - so each time I select a HELIX preset - the HELIX selects and sets the EVENTIDE to my desired EVENTIDE sound - which I can program in or out in different "snapshots" of each HELIX preset
3) The
Boss RC-30 with FS-6 footswitch - yes, the Helix has a looper built in, but I wasn't sure I could reliably use it while playing live in the same way as a pedal looper - and this way, I can change the entire Helix patch while capturing loops from the entire pedal set up - so I could record a loop at lower rhythm volume with certain effects - then, switch to a LOUDER Helix "solo" preset with a completely different set of effects with which to "solo" over the running loop - or, add completely different sounding inputs into a running loop by switching between HELIX+EVENTIDE sounds...this is a pretty limitless set up.
So for me - single stomp delays fell by the wayside long, long ago - but if you are gonna have one - there is probably NONE better than the Boss - I had an original DD-1 when it came out - which boasted an amazing ONE SECOND of delay at the time!!
Great boxes, those.
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I have never owned an 808 OD pedal - but it's my understanding that really - there is not a lot out there that is BETTER. I'd stick with that - unless you WANT something else - in which case, you can get a HUGE array of different OD choices (not to mention, fuzz, od, or distortion) - and that's best left to your ear - maybe Earthquaker has something you might like, or Electro Harmonix or even good old Boss - personally, I think that MOST ALL Boss single stomps, sound pretty darn good for the money - they are usually better quality, and better sounding - than many of their competitors old or new - they are just GOOD pedals. I have about seven or eight of them still, and a number of them are living on my home/for fun pedalboard.
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I bought the Roland GR-55 synth but really no idea how it compares to the GR-20 - but I would say this about my GR-55 - it's a "Closed System" so you are stuck with what it can do - and that is it. Having said that - it contains some great sounds - and some, not so great. The ten sounds that are amazing - are AMAZING. I love it. But I don't find it to be that great for it's regular "guitar sounds" and the synths sounds are hit or miss depending. I find myself using it less and less. But it may be a good alternative to the 20 if you are thinking of retiring the 20 - you should at least listen to the 55 and see if you are interested in what it can do - a bit pricey, but I like it.
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The rest - I don't know - but I wish you luck - I love stomp boxes, and I wish I had a LOT more of them. I have lots and lots of them on wish lists here and there, but if I live to be 100 I will never have time to buy and try as many as I WISH I could. If I won the lottery...I would have HUNDREDS of stomp boxes, I really would. One for everyday of the year, at least.
Good luck and enjoy - you have good kit there - make use of it - play!
Best regards
Dave :-)