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You can run any effect in front or in the loop, save for distortions which can cause damage in the loop. @ICBM can expand on that.
Personally I think you should try a DD7.
Other than that, generally there is very little difference in suitability for going in a loop between analogue and digital - although digitals that run the whole signal (rather than just the effect part) through the A/D/A converters can cause trouble in parallel loops with latency - but so can analogue ones with phase issues. Both are fine in series loops.
As far as I know all Boss delays keep the dry part of the signal analogue and don't run it through the converters, and they don't have phase issues. I'm not totally sure about the RE-20 Space Echo pedal - that does something on the dry part of the sound as well, so it's possible that it does digitize it.
"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Only two things are infinite - the universe, and human stupidity. And I'm not sure about the universe." - Albert Einstein
If you don't want it I'll take it off your hands
Tbh, anything in a single stomp enclosure is going to be fairly simple and straight forward. I'd avoid the Timeline, DD-500, Flashback X4 and Triple Delay, for your needs OP.
There again, I like to actually hear my delay!
We'll, ahem, obviously the bottom has dropped right out of the market for used DD-200s at the moment, but I'll try and help you out