Ok fellow Pinsider's I have a question.

I recently moved from Atlanta Ga. to Jacksonville Fl. a little over a year ago and within the past few months I acquired my first pin. I have always been a vid person up until such time when I realized that arcade games are for the most part the same thing over and over. After picking up my CC Hollywood I was hooked. I quickly got online and not only found a massive community here in Fl. for pins and arcades but we have a very large and diverse group of people here as well which most are very caring individuals. On some of the forums that I read here I'm always seeing people mention in the FS/FT section, " if I only lived closer, I would pick that up. " I understand that half of the people making that comment might be doing that to help the seller or the moral but I'm pretty sure several of them would actually pick it up if they had a means of conveyance. Which brings me to my topic.
My wife and I have decided to run a transport business. We have decided to run from Florida up the east coast. But in doing this we do not have scheduled runs. I work for one of the biggest and most well recognized logistics companies in the US. My company does NOT transport arcade machines or pins. highly due to the fact that they are " high claims items. " I understand that most of us are pretty meticulous when it comes to our machines. I have heard many horror stories of people using logistics companies that have damaged their items somewhere either at terminal or in transit.
So my question is this, would you be willing to pay a little more for an insured company who can accompany you and your time schedule and guarantee that your item(s) arrive just as described or would it be more beneficial and cost effective to wait a week or month. Just curious to know.