Hi Joy,
Actually, my DH and I got pregnant in the first month of trying... so it was actually easy to actually GET pregnant, lucky us! The hard part for me was getting ready to start trying. My A1C's had been hovering around 7.0-7.3 for years and my doc really recommended getting them between 6.5-7.0 for 3 consecutive tests (9 months) before she'd give me the green light to start TTC. Work stress, other stresses, busy/hectic schedules, irregular eating, and some emotional hangups on getting pregnant all added up to it taking over a year and a half of trying to get that first less-than-7.0 A1C.
What i was told, and I'm sure your doc would tell you, was that before I'd get a the go-ahead to start TTC, my sugars had to be well-managed (you and your doc decide what that means for you), any other complications had to be managed and stable (in my case, mild retinopathy), I had to have a healthy BMI, I had to discontinue my cholesterol meds... those would be the basics. A strong healthy relationship with your boyfriend (or maybe fiance/husband by the time you're pregnant) will be key, as diabetes and pregnancy are stressful enough separately, let alone together. He'll need to understand how he can support you through the process, and you'll need to know how to communicate that to him.
What else... I have a pump and a CGM that help me keep tabs on my sugars. If you don't have either of those, ask your doc about what it would take to get them before you start TTC. Start taking prenatal vitamins sooner than later, they won't hurt you if you take them before TTC. I am blessed to work in an education system that provides really really good PPO insurance to its employees, so my supplies, insulin, pump, CGM, and specialist visits (endo, eye doc, gyno, etc) are all covered. I don't really know how to answer "how much" insurance I have -- it seems I have all of it! (haha)
Other details -- I just turned 33 so while I"m not "old," several of my child-bearing years are already behind me so my docs will be thinking of that too as we plan my care. I've had T1 for 21 years and been on insulin the whole time. I have some very very mild retinopathy but no other complications so far, knock on wood. This is my first pregnancy, and I'm just 6 weeks in, so I haven't had my first ob-gyn appt yet.
So far, I have to send blood sugar #s to my doctor's office every week, and I have to get A1C's and thyroid checks every month. Later on, I'm sure I'll have more doctor visits than a non-diabetic pregnant woman would, especially in the last trimester. I'm writing down everythign I eat to make sure I'm getting enough calories and nutrients for my little one, and that's mentally tiring. I'd say that emotionally, you have to be ready to tackle some of the toughest diabetes management you've probably faced to date. it's totally possible to have a healthy pregnancy with diabetes but it will be hard, and getting ready to deal with all of that was really, really hard for me(let's be honest -- I needed to grow up a little bit). But now that I've got someone growing inside me, it's easier to stay motivated and take it a day and a week at a time.
I'm starting to ramble now. Hopefully that answered some questions. I book you might enjoy is Cheryl Alkon's "Balancing Pregnancy with Pre-Existing Diabetes." It's on Amazon and I picked up a copy a year ago, before we started trying. It helped get my mind sorted out on a lot of things.
http://www.amazon.com/Balancing-Pregnancy-Pre-Existing-Diabetes-Healthy/dp/1932603328
Good luck!
Amanda