I was in a similar boat. I ran in college and then shifted to cycling for similar reasons. I worked my way up to Cat 1, but now I do a fair bit of trail running because of convenience.
1) bike - I’d recommend getting a middle of the road ~3k bike from a place like Canyon, Lauf, etc (great value for the cost because it’s direct to consumer). Getting a decent bike goes a long way and saves you wanting to upgrade. I’d recommend a gravel bike and if you want to go crazy get another pair of wheels for just road. You can always switch out.
2) gear - buy a good pair of bibs (well, a few). Bike gear can be outrageously expensive, but there are almost always deals / discounts available. You don’t need to wear rapha - if people care what you’re wearing, they’re probably not worth riding with.
Also, I’d recommend a head unit like garmin or wahoo for navigation / training. These are a must have in my opinion.
3) racing - American road racing is dying and in crits you’re guaranteed to crash eventually. Gravel races are everywhere, though, and can be fun once you’re more comfortable riding in a group. Racing for local KOM’s and even Zwift racing can be fun.
4) convenience - zwift is the most convenient if you’re a working person with a family. You also don’t need to worry about cars. I’d highly recommend a good trainer and I can probably share a 40% off discount on one if you’re interested. Zwift Hub seems to be the best option, though, in terms of price (not with a discount for another one) and ease - universal cassette. So I’d probably recommend the Zwift hub. Why Zwift? No route planning, no getting to a good stretch of road for 30 mins, no coasting, just hop on and ride.
5) don’t forget about running - as I mentioned, trail running has been great for me. The varying terrain makes me less likely to be injured and is a great way to mix it up. Plus, it’s such high aerobic gain for the buck. Not to mention, the running community is just a lot nicer, usually.
6) time - if you want to be competitive in cycling, it’s a looot of time. 10h a week as a runner puts you in the highest category. 10h a week as a cyclist puts you at average at best, where the top rides 15-20h+ a week. That being said, if you train smart you can usually be quite competitive off of 10h / week.
7) runners in cycling - typically have great aerobic fitness and climb well. Learning how to ride in a pack plus improving muscular endurance / snap will probably be what’s more difficult.
8) Fueling - fueling is important in cycling and makes a huge difference on performance. Even if you don’t think you need it, eat and drink on the bike. Not fueling enough held me back for too long.