I'm so sorry for your loss. I wish you luck and peace as you TTC for a lil' sibling.
Were these past 5 cycles pretty "normal" for you? We did used clomid (and other measures) to conceive our 2nd. In our case we weren't ovulating or cycling at all. I was charting so knew that, but ya know doctors, they don't believe charts, just wanted the labs, and what do you know... that confirmed it

.
When it comes to fertility treatments clomid is pretty "benign"- I wouldn't be worried about taking it without blood work- the bloodwork would either show you're not ovulating and so they'd give it to you... or you are, but still having difficulty so they would probably write you a script anyway since it was previously successful.
But that's me and my comfort level- what's important is yours. If you're unsure it doesn't hurt to give the office a call to get peace of mind. Doing something to make yourself feel more comfortable is always worth it.
If you do decide to go ahead with it- I hope the side effects are mild! Gosh I remember that stuff making me bonkers! I called it clo-MOODy... cause whoooo!

Good luck!
Lauren