BColl_Has_Too_Many_Shoes
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All good points, but I think there is an option between MTM with house fabric and $3500 bespoke and it may be what @gimpwiz is looking for.
He doesn't wear suits much, but when he does he wants it to look great and be able to count on it for a while for special occasions.
Something like Tailors Keep (which I think counts as 3 fitting bespoke not MTM) gets you substantial time with a good tailor to help with the vision issue mentioned, a great fit, and branded fabric. There is one round of adjustments built into the $1700-3000 price they gave me.
Another option is the Hong Kong tailors that travel through the bay area, which can shave the cost down to $1200 for a canvassed suit with a fabric like VBC. HK is a bit of a minefield, but there is a whole thread to help you navigate it and there are some great low cost options. (A major portion of process of making your suit will occur in China)
My personal opinion is an emphatic yes on the waistcoat if it doesn't bust the budget after you've settled on the suit you want.
I would only say that spending so much money on a suit ($1000+) seems a bit much, especially when you consider you are not entirely sure how the suit should fit. I don't mean fit in terms of measurements. I am referring more how you interact with the suit.
I just feel you can probably pick up a Navy SC, as suggested by @dauster, to experiment with what feels comfortable but looks good. Two key parts of a suit are fit and comfort (color being the third critical component).
Just wouldn't want you to get stuck with a suit that looks good, but then you repent spending all that money when your comfort level isn't there. Once you've nailed down your measurements, you could always do a versatile Navy SC followed with maybe a Dark Grey or Charcoal suit for the $1500-$1750.
Also be aware, you may want to purchase a nice new pair of shoes to go with those new threads. Leave a few extra coins for a pair of leathers (completely biased here but shoes make the outfit ??).