We have made day by day ressies twice, the reason the 1st time was we were booking at VWL during first weeks of Dec., a very popular time at this particular resort. It is a little annoying doing this, but once MS knows this is what you are doing, they get you through promptly. Just let them know up front your intentions. They will help it go smooth from there.
Last time we booked day by day, I forgot to call for 5 straight days. I was so relieved to know that this was no problem. Our ressies were intact. We are going in Oct. during F&W festival and were concerned that our home resort would be booked as this seems to be a popular time among DVCers also.
Honestly, you will probably be OK calling and making ressies all at once, but if you dont want to risk it and be sure do the day by day and be safe. This wouldnt be a everytime you make a ressie occurence, just when pts are low and season is high. We just booked OKW for Mar. and were willing to travel whenever they could get us in. To our surprise, it was wide open,"which week do you want to come" was their reply. But the pts are pretty high then.
As for the day by day, call MS, ask them what you should do. If you get a knowledgeable CM, they will know exactly what you are talking about. Tell them the dates you want to make ressies for and they may even tell you the day you need to start calling. If not, there is a website that I cant recall, but I know someone on here will give you that info that can calculate the exact day you need to start calling.
Another little tidbit, when calling MS to make ressies, after dialing the #, touch 3, wait for the prompt, then touch 3 again. Also MS opens at 8am Mon-Fri. Call right then if possible, a lot less wait time.
Sorry for the long post. Good Luck!!