1. You would need to create the same amount of blocks via PoW, by altering the timestamps you can make it have higher difficulty. Note here, that if you have less hash than was put into the original one month, then it would take longer than one month to produce a more difficult chain, could be much longer... and thats actually I suppose the point that the OP was making originally (at least one of the points).
What if I had 100x the original PoW Hash?
I am wondering if it could be done in much faster than 1 month.
If so would this not also be a threat to PoW Chains without a checkpoint?
