While I completely agree with everything you said, it doesn't sound like the OPs family member has a lot of dough.
Rosen is very expensive. You aren't getting out there dropping anything less than a grand (and it goes up (way up) from there. Even their outlet store in the Heartland centre is more expensive than most other places.)
And, the one thing I hate about Rosen's is the SECOND you walk in the door, the sales people are on you like a buzzard on a gut wagon. And it's upsell upsell upsell from there. Drives you mental. But they do have very very nice stuff.
I know what you're saying, but all stores are like that... I just deal with the guys I have history with when I go there (or another shop). It becomes more relaxed over time. They can help quite a bit.
Circumstances and situations aside, I suggested Harry Rosen as they're easy to find if one's budget allows. A local shop, etc. that can suit your needs could be a better choice. Fit is what is important. If Tip Top or Moores is where the OP's budget is at, then that is where they are. Everyone should do their best, no?
For everyone as a discussion item and without getting into what we all do for a living, in a competitive world, do you not find lack of quality clothing to be a detriment? A cheap sport jacket and suit 100% stands out from a "quality garment". Men know and women can tell. Sock a bit a money away and over time, you should have enough to buy a sport jacket - especially when the end of season sales comes... Rinse and repeat those steps and before you know it, you'll have a wardrobe.
This process helped me. I definitely believe it helped in raising my salary.