Follow up on what I actually bought:
Although I had planned on working my way up over time, my wife was on board to go straight for Paulsons after playing with the Jacks sample set.
I ended up following
@MoeTremper's suggestion and buying a Horseshoe Cincy 500 set from
@The Chip Exchange.
I also got a rack of Jack quarters from
@Apache via
eBay, and have a barrel of Jack 100 secondary (not pictured) coming in from
@justincarothers.
Having a 500 set plus a rack I got a 600 chip acrylic case for display/storage. As I get more I'll probably get a 1000 chip acrylic case, a metal case and who knows what else. I also have 12 Paulson trays on the way as well.
Overall, I'm very happy with the chips I have so far and the helpfulness and kindness found on this forum! Since Jacks were what my wife and I really wanted, at first I wasn't sure about the choice about the Horseshoe Cincys, but after having both I'm glad I got them. I love the Jacks, but they feel and look so good mint, that I'll probably keep them mainly for display and only pull out for play on special occasions. The cincys look really good too, design-wise, and are casino used, so I won't feel bad using them heavily. I guess they will be my chip equivalent of a daily-driver (weekly-player?). Over the next few months I'll be trying to source the following Jacks: 200 $1, 200 $5, 20 $100 primary. I'm not in a rush atm, so I'll just browse the classifieds as they popup instead of posting a wanted ad.
Thank you again for all of your help guys!
Pic: my starter walmart suited set, a rack of sample sets I acquired during research, my case of cincys and 1 rack of quarter jacks.