Introducing a puppy to an older cat

My boyfriend and I just moved in together about 2 months ago and my older tabby cat is finally adjusting. He has some issues with change and is a little skittish (don't know why, honestly). We really want to get a dog, but not sure about how my cat will take it.

• Charlie is 8 years old
• Has all his claws
• Is not on medication
• Has lived with a dog in the same house before. The dog was a golden and a bit older. He never was in my part of the house, but it had a large backyard where he ran around on a leash and Charlie would be on his leash on the patio. They could not reach each other when both leashed, but could get close enough to sniff from a short distance. He took that fairly well after a while and could be outside when the dog was out and not be worried.
• Lived with a terrier breed in the same apartment recently. Charlie was about the same size as this dog, but was not happy about being in the same place, I think because this dog has tons of energy and wanted to play a lot. He tolerated after a while and after about a year (or less), they would co-habitate in the same room easily as long as the dog was laying down or not energetic. I blocked my door to my bedrooms so Charlie could get out but the dog couldn't get in (dog peed all over everything I own) so they were separated when wanted.
• Met my boyfriend's older dog (a border collie). Charlie hissed and was not happy about meeting her. His dog generally didn't care at all that my cat was there and is gentle but a little excitable when she sees people she knows so I think that's why he wasn't happy. We tried to introduce them a bit more here and there but mostly Charlie would just hide.

We're not sure how he would handle a puppy or a new dog. He's kind of back and forth about it but I don't want him to be miserable. We're kind of leaning towards waiting until he passes to get a new animal but would love to introduce a new pet into our home and give it a great place to live. Any advice? Tips or suggestions?

Thanks!

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