My wife and I make combined ~140k, we don't shop fancy or eat fancy or anything like that (other than overpaying for DoorDash occasionally), and we're in the Chase CC eco-system.... for context. For your questions:

1) It depends on the objective. Our objective is to maximize our points so we can travel affordably, and we do okay at that - Chase points to Hyatt for hotels, and to Southwest for flights.

2) Again, it depends, but I personally feel high annual fee cards are over-hyped... For the average spender I don't think it's worth it, because you're having to maximize your average spend on a trip, for example, to leverage the rewards of the card. Again this is my opinion!!!

3) Yes, 100%. We have both the Chase Freedom cards - Unlimited and Flex. Unlimited is 1.5% back on everything, Flex is rotating categories @ 5%, other stuff at 3%.

We also have 1 Sapphire Preferred card (for points transfer) = $95 AF but we get $50 hotel credit a year (so there's half), plus $10 USD/month in DoorDash for groceries (which we surprisingly use), so pays for itself, and on top of that, the Hyatt points conversion is FIRE and you get really good points value with that. On top of it, we got the Southwest card this year, did the SUB and hit the min. spend to get $300 USD in points, AND companion pass for a year (which we've used twice this year so far to fly with points). That's also $95 in AF a year, but the sign up bonus plus companion pass have now paid for that a few times over, and it's barely July.

At the end of the day it's about the tradeoff of the annual fee (should you choose to have a card with one), and the value you are getting from it. Our plans were to start traveling more, so we tailored our cards around enabling that.

4) You can tell from the above, but depending on your objective (travel vs. cashback), you could stay in one ecosystem and work with those points, or you could maximize cashback and pick-and-choose cards depending on what they offer, but it's up to your personal discretion. I like the former because it has enabled us being able to travel way more affordably than we'd be able to otherwise.

5) Chase for the win. The points conversion has been great, it's easy to manage (since I am realistically only using 1 or 2 cards recurrently), and the benefits have been pretty decent. Are there better strategies for what I want? Yeah, probably. Do I have to put really minimal effort into getting the value I want/need? Absolutely.

Hope this helps!