When should I test?

Now onto my question/situation. I had the mirena IUD in for almost 6 years (yes a year too long). It "expired" last September. I just had it removed on 6/14 and started on ortho tri cyclin. That day my de did a pregnancy test (negative).  My hubby and I did have sex the day before I ovulated which was a week before the removal. My period is now kinda weird, brown spotting 6 days early. Ik my body will be weird for a while during it adjusting to the change. I feel like I should take another pregnancy test. If I got pregnant on 6/4 would the drs test he did on 6/14 be positive? Should I test again just to be safe? And if so, when? 

On the calendar below, the heart represents when we had sex and the flower represents when I could have ovulated. Remember, my IUD was 9 months passed the removal date, but not neccassarly expired.