(They’re so small as to be like a speck of dirt so i can’t see them in the finished paint job at all, I just know I brushed over them while cutting in!)

As long as the dent isn't in the front panel, it should be fine.That said, depending on your area, that may not cut it.

Ideally, I'd want to cut them in on the deal to align everyone's incentives. 

I have them pre-typed out in a word doc and just cut and paste, saves a ton of time. 

After listing my property (a 4-plex in San Diego) too high in a declining market, receiving no offers after a month even after a 9% price cut, I asked my broker: at what price could he guarantee an offer within a week or two.

If it cutting into your profit, you need to raise your rates to compensate.

I fear that the upcoming bailouts and cash give-aways by the federal government because of the corona virus will affect the markets in many different ways.I am terrified that printing/creating trillions of dollars will cause my $60,000 cash to be cut in half or more in real dollars by inflation.

However, sometimes having a lot of resources can get overwhelming and I would like to stay laser focused in my pursuit.

So....... how do I know if he has my best interests in mind or if he is trying to cut corners to make his life easier?

If you think there are short-cuts to building wealth, you're going to be disappointed.