Advise please! (Sorry my post is so long)

My last period was from April 26-May 2nd. I didn't start using the ovulation things because I hate trying to figure out the lines but I found some of the digital ones and starting using them on May 10th. I went to the doctor on May 12th and she estimated I would ovulate the following week. So I took an ovulation test everyday since the 10th and they were all negative. I was starting to get frustrated and upset because BOTH of my period trackers said I would be starting my period the fourth week of May. I was feeling discouraged and didn't want to be upset again so I didn't test for a day or two. I tested on the 26th and FINALLY had a smiley face. So my husband and I had sex. 

Now I don't know how long to wait before taking a pregnancy test. I don't know why ovulated so late in the month when I thought my menstrual cycle was going to begin. 

So my questions are:

When should i take a pregnancy test

And is it possible to ovulate more than once a month but not back to back? My sex drive was increased between May 3-9, so I thought maybe I had ovulated then. 

Thoughts?