You can not earn points for all rooms (it's the most popular question here).

A Member may earn Base points for up to two rooms per stay, if all eligible charges for both rooms are paid on one folio. Base points will be earned for all eligible folio charges incurred on both rooms. The term “eligible folio charges” is defined below. Bonus points issued on Base points, including tier bonuses (15%, 25% or 50%, depending on member tier), bonus points earned through the HHonors Points and HHonors Points Earnings Style and double or triple Base point promotions, will apply to the total Base point credit earned for both rooms. For any other bonuses, including HHonors Marketing Partner bonus points and other promotional bonuses, bonus points will be awarded on one room only. For purposes of obtaining tier status, a member may receive one stay credit on one room only. For purposes of earning miles for stays, miles may only be earned on one room only.

You realize your overlapping stays will probably be combined into just one stay no matter how many times you check in and out of the same property, right?

Just to double check, I'm assuming you are also doing a fast track or some other promo for gold, as the counter will reset to Zero on Saturday and any stays towards gold you have on Dec 31 don't count after Jan 1.

In any case, your status will not take effect until the credit stays and the system is updated. I think they will charge you for the internet, but you may be able to get them to waive it once you have the status if you get it during the stay. This is something you should discuss with them first and not try to do after the fact if they say no.