The short answer should be, yes, there is something that can allow you to differentiate individual feathers at 5000' and if price (and weight) are of no concern then I'm certain we can figure something out.
I find the review you posted to be quite thorough and well-written except I found the title a bit misleading. I think it should be Catadioptric (or mirror) Scopes since they are the same, not in competition, but that's just the editor in me.
Questars and TeleVues are always excellent, but can they do what you want? The article says the Questar 90mm can resolve 1.31 arcseconds. I guess we're going to have to do some math! I will post another note here soon with that calculation.
Maksutov-Cassegrain designs are generally excellent bang for the buck. My 70mm is a Mak, the Questar is a Mak, the new Celestron C90 is a Mak. The reason is that it is a simple yet robust design. Frankly I'm amazed that there are still Schmidt-Cassegrains on the market but I think time will tell. A good pair of astronomical binoculars might be a good option--binos are generally much easier to use, but (very large ones are) harder to carry.
I think you need to tell us whether you intend to carry your solution around with you because size and weight may be the deciding factor if price is not.
I think you're asking an interesting question and am anxious to work on it!
Robert