When should I test?

Sorry this might be long but I need advice. I turned 40 in October, hubby and I have been trying since 2009, we have given up and said if it's meant to be, it will be... fast forward may 16th 2019 o got told I was pregnant but my levels were 13..so come back in 48hrs, again 13... after being poked several times, may 27th I spotted and was told I had a chemical pregnancy. Went to my OB she said we could try again as soon as were ready, I bled till that Friday and as soon as it stopped hubby and I started trying again. I've been tracking with my fit bit since April when my cycle went MIA for 2 months which is normal since I was on depo as a teen and been jacked up ever since.. I know I can get depressed & obsessive on wanting this so bad.. it would be a first for us both... should I just wait and see or test and get let down knowing how hurtful it can be?