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+1 for the HEQ5 & ED-80 - great combination, which would be popular if & when you want to sell to finance an upgrade.
You are probably going to need an Autoguider as well to get nice round stars - you can modify a finder scope, but allow another $3-400 all up.
What sort of long lenses do you have - you could start with some wide-field shots with a 2-400mm camera lens.
I don't think you want to consider de-rotation - it means that you have to have 3 motors (alt, az and rotator) working in sync to track an object. Sounds good in theory, but probably best left to professional observatories with price tags in the gazillions.
DT
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