If you are sending to the same address, every time 1 CGB is sent to it, days are reset to zero.
If you send 1 CGB to a separate address every day for 30 consecutive days, you will have more chance to get POS blocks over the next 30 days after the first address becomes eligible for stake. Some addresses may take a few days, some less, some more. You wont be guaranteed to get a block every single day, and you wont be guaranteed every address will get POS within those 30 days.
I would advise everyone to do this, or split their funds to create more POS blocks. Doing this will help secure the blockchain and keep transactions moving as the POW mining reward dwindles
Although you have the said 30 CGB spread between 30 addresses and are hitting more POS blocks, you are still receiving ~2% annually on those 30 CGB combined, whether they are in separate addresses or not.