Depending on how motivated the acquirer/investors are, you can push back a lot on due diligence. Not in the same sector, but an immediate example that comes to mind is Bernie Madoff. He let his investors do almost no due diligence. Many walked on this condition, but more than a few $billion just closed their eyes and bought.
It all comes down to how best to spend your time. Is every minute spent pre-organizing stuff for a probability of a DD better spent in front of customers or with your engineering team? If so, then don't be too concerned too early. Of course, if the exit plan from the day 1 is to sell to a larger shop, then get those books/records in order from the get go.
There's usually some leeway in the strength of the representations and warrants. As seller you want them as weak as possible. You want minimal grounds for the buyer to come back later and claim, "You promised X would be true but it turned out not to be; and you agreed you'd make us whole". Instead you want the deal to be done so you can move on with your life.
The more complete your due diligence materials, probably the more you can negotiate the R&Ws to be milder and more reasonable for you. Or even if you can't, at least the R&Ws are covering less unknown territory.
Whereas if you have big holes in your documentation, naturally the buyer will want you to be on the hook for surprises, and may require some proceeds to be set aside in escrow, or whatever.
It all comes down to how best to spend your time. Is every minute spent pre-organizing stuff for a probability of a DD better spent in front of customers or with your engineering team? If so, then don't be too concerned too early. Of course, if the exit plan from the day 1 is to sell to a larger shop, then get those books/records in order from the get go.