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I won't spend more than 30 minutes trying to sight difficult objects. Basically, if I don't see several fleeting glimpses of the object in that time frame while trying a number of appropriate magnifications, a black hood and jiggling the scope, I will consider the object out of reach and move on. If there's a couple glimpses of some fleeting variation in brightness with long intervals inbetween, I still won't call it a sighting as it could be just "visual noise". But, if I catch several glimpses intermittently, then that tells me it's a real object wavering in the seeing.
Spending too long staring intently into the eyepiece desperately trying to catch that glimpse has its own pitfalls - averted imagination, eyestrain, visual noise, discomfort sitting/standing in one position too long etc.
To get the best chance of seeing on-the-edge stuff, I'll try and time my obs for after 11pm and when the object is within a couple of hours of the meridian. The latter is less of a concern if it's a far southern target, but when approaching 0* dec and into the northern sky it becomes pretty crucial. All my eyepieces have 20mm ER and feature at least 65* FOV as my scopes are undriven.
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