Sometimes you just gotta start somewhere and well...get started. Most of us do not know what we want when we first start off and we certainly do not know which brand(s) are better or even what types of gear is ie jacket styled vs bp&w or back inflate.
I think you will end up renting a lot of gear...using some borrowed gear to start to figure out what you like or don't like and THEN figure out if you are staying with the sport long enough to change out the initial gear you purchased.
Yes there are advantages to buying a pkg deal and for many divers you won't go wrong. If its a long standing shop that will service and repair the sale then go for it. If you have some of the major gear already then obviously adding add'l gear is different.
And as you said...there are NO WRONG ANSWERS...just good things to consider.
For example... as we come off any dive season or the end of the year...some manufacturers discontinue one model and offer a new one. You can get some great deals on a brand new but discontinued model.
Or a shop may have (1) size and (1) model left of an item and is willing to give you a great deal to move it out of inventory due to all the overhead of taking up retail space for (1) item.
Both of these are a great opportunity to have good quality gear at a great price. That's a WIN WIN in anyone's book. How do you know? Well you start now but researching and reading about brands... and ask questions and then when you see a great deal you can jump on it.
ONE CAVEAT: When we say research we mean online. Please do NOT go to your dive retailer and ask a ton of questions about gear and try a ton of things on and then wait for a deal to show up on the internet. Well I guess you can ...but please go and give the retailer something for all the free education they gave you. Or better yet... reach out and show them where you found the better deal for the same gear online and see if they can meet you part way. Remember it costs about $10 a month to host a website and hundreds or thousands a month to keep a dive shop running. Oh and the internet can't put your gear together for you....or custom fit it to you....or teach you how to tweak things just so....or repair it...or service it. And guess what? Neither will your local dive shop if you did not get it from them. Sure some will change you more than what they normally charge when you buy from them but that's fair too. After all...try and get the internet to service something for you or repair it? It doesn't work....trust me I've tried.
So when we say DO YOUR RESEARCH we mean ONLINE...not in your local dive shop...unless you plan to buy from them or give them a chance to work with you on an online deal.
One other thing... sometimes online dealers sell below the manufacturer's suggested pricing giving them an unfair advantage. So by working with your local shop dealer you can more readily work out a deal with them and that's cool! If it weren't for local shops and local instructors most of us would not be certified. So try and pay forward for the next group of divers who need dive shops to be in business so THEY can get certified. Its as important as working to keep the ocean's healthy and taking care of the planet.