Photographer Issue

No I definitely get your frustration. If he is unresponsive now, the last think you want is him to be unresponsive around your wedding. Have you asked your dad to reach out to him? Do you think that’ll make a difference?

I get your frustration too because he seemed unresponsive before his foot

Well, the good thing is he's a family friend - so you should be able to at least ask for some of the money back because an engagement shoot is not worth $500, (especially considering the time delay, etc.) and it doesn't seem like he's attentive or will be very good for your wedding. I would definitely work with someone else. That's why family/family friends aren't always the best option!

Honestly, eat the $500 and look for a pro photographer asap. Browse Thumbtack.com or the vendor tab here and make sure to read reviews.
Explain to your dad that you have a legally binding contract that his friend has not honored and let him figure out how to deal with it because he has a closer relationship. A professional will be more punctual with communication and other duties without undue stress.

I would give your dad a heads up that you're going to request a partial refund and you'll be hiring someone else for the wedding. That way your dad can figure out how he wants to handle the friendship going forward. Next, compose an email that states you're requesting a refund of the deposit, minus the time spent taking photos, since you haven't recieved the photo files as scheduled. Since the contract hasn't been fully executed (signed by both parties), you can feel confident in backing out. Then go ahead and start looking for someone else. It may take some time and a lot of emails, but hopefully you'll recoup some of the cost.

Also, lesson learned: don't send money until contract is signed/at the time of signing.

Hi, I am so sorry you're going through this right now! My fiancé and I went through a similar situation with a family friend who we hired to be our photographer. She also seemed to lack interest and it was the same thing where she was really busy all the time. Long story short, things fell through and we decided to hire another photographer. Unfortunately, sometimes it seems like having a family friend also be a "wedding vendor" makes them think they can slack, but you're still a client at the end of the day. I find it more professional for them to treat you just the same as their clients with the added bonus of being friends. These photos are going to be something you cherish and look at for the rest of your life, they should be taken by someone who genuinely cares about capturing your day, and it doesn't seem like he is that person. Also, if he broke his foot, isn't he probably resting more than usual?? Like, I don't know if that's a good enough excuse in my book. Also, having clients booked and then saying "hey gotta cancel, family vacay" is suuuuper unprofessional. I hope you figure it all out and find a photographer that captures your day the way you want it!

I totally understand your frustration. We are using a caterer that we used for my sister's wedding and that we know through church and it's been a headache. I'm 19 days from my wedding and I'm still waiting for a response about final numbers and final details. It's very stressful so I would highly recommend looking into other options