Despite the siren song of higher profits, you never see people sell the class A/B portfolio and more down in class.2.

The only indicator of how the financial information was used, was to generate a pricing quote -- and the perception of that is depending on you have little or much you have, you pay more, or less (I could be wrong here, but that's the perception). 

I personally have certain amounts I act on so then tenant doesn't get the perception I am nickel 'n dime-ing them every month.

When your having your doubts just keep pushing toward your goals and doors will open up as your mindset and perception changes.

I don't own in Hawaii, but my perception from my research there is that it's not an ideal cash flow market right now but can be great for appreciation, which it sounds like would be a pretty good deal in your scenario.If I had that much cash to deploy personally I would be putting it into properties that are most likely to hold value and most likely to gain value. 

There is a perception unique to Finance and Real Estate folks that rates will be lower in Q4 of 2023. 

I think khakis and a buttoned-shirt fits pretty much any situation, adjust based on what you think the neighborhood/seller would expect.As to arrogance, there is exuding arrogance and there is the perception of arrogance. 

Changing the perception of this breed is hard work as well.  

Real or not, that is the current perception in Chicago.  2.

Lastly, perhaps changing your perception to their negativity may help.