Quoted from yancy:
I used to play poker semi-professionally and regularly carried more cash than most pins cost. Not at all a brag, it’s just the tool of the trade. Makes you pretty numb to the novelty/fear of carrying cash. Pinball transactions feel very routine.
I am the same way. Over the years I have made plenty of "cash deals" in the tens of thousands of dollars and never really worried about it. Like anything else if you are used to doing something you worry a lot less about doing it. For years it would drive my wife crazy when we were headed to pick something up and had $10k or $20k in hundreds along with us. I have been dealing in cash for over 50 years and to me it is just a pile of paper.
That being said you don't wave it around, you don't leave it laying on the front seat of your vehicle, etc. I have never carried a gun because I doubt I could shoot anyone - I am just not that kind of a guy. I know it is a huge risk not carrying but I also know there is no point in carrying unless you are willing to pull the trigger. There have been times I was a little concerned and I have actually driven to peoples houses and driven home without even stopping but if you follow your gut feeling typically you will be OK in the end.
Now that I am getting older I am kind of glad those days are more or less behind me. I just don't know if I could bring myself to carry some of the huge amounts of cash I have handled over the years. Under $10k doesn't worry me all that much but once I get over that it starts to freak me out a little these days.
Google Maps is your friend, do a little homework on the area you are heading to also helps, get a feel for the seller, follow your instincts, and proceed with caution and typically everything will end up fine. But in the end if necessary just give up the cash instead of ending up dead if that is what is necessary. Cash can be replaced but once you are dead it is over. And remember having a gun is pointless unless you are willing to use it.