Yes you can enter as many times as you want as long as you don't go pass the 30 days. No limit how many times in a set time frame.
If you want to stay longer than 30 days you can get Extension of stay up to 59 days which is easy to get. Just don't forget your return ticket or you will not be able to enter.
After that it easier to do a Visa run leave the Country and come back in. If you are going to take your partner with you on a Visa run, make sure she has all the Documents required to leave the Philippines or she will be stopped and not allowed to leave the country. I have seen this happen so many times
Once you are married to a Filipina than its easy, you can come and go as you like, as long as you don't stay longer than 1 year.