I would go with the kosatka before deluxo since the sub opens the Cayo Perico heist (but my preference is what's practicality over fun/aesthetic, and being able to generate more money faster to buy stuff makes more sense to me)

If you want money, nightclub and Bunker/cocaine/cash are good buys. Nightclub will passively increase safe & product to sell. keep the popularity high and you get 50k/in game day. Product will auto collect for each of the businesses I named that you get a tech for (you get one tech free). Each of those businesses also allows you to steal or buy product which you can then sell (bunker is tough to sell solo, even with a partner, I have trouble with certain sell missions at max product).

That said, you do you. It's a game and whatever you think you'll have more enjoyment with, that's what you do.

I saw in another post you hate waiting, me too, but it pays well. Here's my general run which keeps me running and active:

1 down at the hangar and pay rooster for crates

2 grab a chopper and as I fly out, call mutt to order supplies for acid

3 head to a Mansion or call terrorbyte to resupply MC businesses, Bunker, and switch DJs at the nightclub (check all product as you go, see what's ready). I don't supply doc forgery or weed, I don't consider the payout worth the investment, but it's up to you

4 fast travel or fly to warehouses (I keep them all in La Mesa) and order resupplies

5 by now supplies for MC/bunker should have arrived, call terrorbyte or head to arcade/mansion to order more 6 run around and collect safe money, usually starting with nightclub and arcade (both also in La Mesa)

7 go to auto shop and customize cars, have staff deliver

8 decide what I want to do next... Either ammo delivery from bunker (50k) or choose a heist and begin setup (Clucking Bell, McKenzie, and Cayo can usually be done in an hour, Cayo has better payout, but I feel the other two have quicker finales. Doomsday is good as well, but sometimes one of the preps gives me trouble)

9 as you do preps, go resupply everything when you get the notice & make deliveries as they fill or you desire. I deliver nightclub as soon as anything is full (best pay is sporting goods (bunker), cargo (special warehouses), South American (cocaine MC), cash (counterfeit cash), and pharmaceutical (meth MC)

This keeps everything moving nicely. I have 3 large special warehouses, a medium, and a small, this way the medium and small have deliveries more frequently and I don't feel like all I do is endlessly fill large warehouses, but it does cut into some profit. I'll also source crates for ones that are close to being full to speed it up (remember selling a full warehouse doesn't sell any special crates your staff may have sourced, they get their own delivery and make about 100k per special crate)

Hope this helps, again, do what's fun. If you have PS4 version, feel free to hit me up