I always prefer honesty, but in this case I certainly wouldn't find it to be "refreshing."
Actually, in this case (Trump being rich, referenced in the OP) it's very refreshing, and we have concrete examples of seasoned "politicians" not being honest on the same issue. Romney tried to distance himself from it and failed. Hildabeast was either delusional or a liar about being "dead broke". I appreciate Trump saying "hey, I'm rich, I earned it, that kind of money is a lot but to me it's peanuts". That doesn't mean I agree with him on his positions, but that kind of honesty is in stark contrast to other politicians and is refreshing.
As for punishing honesty, I don't see it that way. The punishment is for the sh*tty belief, not the honesty.
Sometimes that's true, sometimes not. Often we know what the politician actually thinks, but we know it's for the better if he/she just packages it differently or tells us a story or does a nice song and dance. I prefer honesty, even if I don't like the message.
For example, we don't withhold punishment for a murderer just because he admits he committed murder. Would you classify that as punishing honesty? No.
In fact, if someone admits guilt and is honest about what they did, the system rewards them for it (plea bargain etc). However, in some ways we do punish honesty. For example, if there's an accident and someone apologizes, they will get held against them in a subsequent suit. If a doctor says "I'm sorry", it gets held against them.... so any lawyer will tell his/her clients "don't ever admit anything and don't apologize". It's sound legal advice, but not good for society as a whole.
