I started at a similar point to you. I was eating pizza 2-3 times a week, aside from that I was eating full loaves of bread (cheese bread from WalMart <3) in one sitting, I was eating cheese bread with my pizza and was also getting a calzone every time I got a pizza so 3 times a week I was eating over 6000 calories a day.
I am 27 yrs, 6'0" tall and started at 320lbs, 43.4 bmi at the end of January and am now down to 281lbs, 38.1 bmi. The first few weeks were the most difficult primarily because my roommate was a bad influence on my diet since he orders chicken wings and pizza and goes to get fried foods for every meal and vows to never eat vegetables.
I also at the same time was a hoarder, so every pizza that I ordered for the past 6 months or more was stacked up in my room along the wall just sitting there... Once I decided to change I kept those there for the first 1 1/2 months specifically to remind me of where I was starting at to motivate me to continue forward.
Similar to you though, I feel like it is often difficult to hit my calorie limit with healthier foods. I sometimes only have 1000 calories due to not being that hungry and am like "How can I get to at least 1200 today so MFP doesn't yell at me?" so I end up at that point getting junk food whether that be a soda (empty calories) or join my roommate on a latenight Taco Bell run and get a shredded chicken burrito (400 Calories).
I was able to fix the pizza problem that myself and my roommate had by introducing him to curry, that pretty much solved the problem of tons of pizza which was by extension causing me to eat all the cheese breads. Now we do a meat (mahi mahi, chicken, or beef) with rice and a stir fry sauce or curry every other night and the nights between I usually have sandwiches though sometimes I will get some Chikfila (the fries there from what MFP says are low in sodium compared to other restaurants so I like that).
Just try your best to log everything. I have only had one cheat day which was one week ago in which I decided to try to eat the foods I used to eat (pizza, lots of fried stuff) though of course in smaller portions... and I didn't really enjoy it anymore. Hopefully you will able to make it and continue forward.
My primary reasoning originally for trying to lose weight was twofold... firstly, someone I know is extremely overweight and his doctor told him he needs to go on a plan for just 1400 calories per day (he is over 6000) along with the rest of his family (his wife and children are similar weights) so when I found this out I decided "Hey, I could do that. Maybe I will do it to show him he can do it too?" though I hadn't started yet. The thing that caused me to actually start is finding out that my last remaining friend that wasn't married or moved far away or busy with work (aka: only person I really talked to most days) got a boyfriend when I was going to ask her out and later she turned out to be pregnant so that kicked my motivation to proceed into overdrive so that I might finally find someone after being single for the past 5 years.
Good luck on your journey and if you have any questions, comments, concerns, challenges just post here and I'm sure the community will be supportive and honest in their responses.