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I pointed out the puddling in the final fitting and he said he could correct it, but this may cause pulling/puddling in another area. Is this worth the risk?
Hm, I'm not sure if we're talking about the same issue. I wouldn't describe this as pooling.
At the back of your trousers, you can see how excess material is collapsing under your seat, also causing the back of the trouser leg to ripple. In the past, I've had this issue corrected by shortening the back rise and letting out the crotch to compensate. However, again, I am not a tailor and would leave it to the tailor. Here's an example what I mean:
Here you can see the trousers falling cleanly at the back. These are fisttail trousers held up by braces, which helps.
But here you can see the same thing for belted trousers. Not as clean, but pretty clean.
It's harder to get a pair of slim trousers to drape well. Your trousers look quite slim.
If I'm being honest, if a tailor delivered that suit to you, I would recommend just finding a different tailor or going off the rack. More than delivering a suit that technically fits well, I think a tailor should deliver something that looks very good. For $750, I don't think that's a bad deal. But you seem to have a standard build. Instead of paying $1,500 for two suits that don't look great, or eventually $2,250 for three suits, of which only one looks great, I think you can just buy a good ready to wear suit. Depending on where you live, The Armoury and No Man Walks Alone both sell really nice models. I think the cuts and proportions are better looking, and you can probably get them adjusted locally to get them to fit right.