This app was mentioned in 3 comments, with an average of 2.33 upvotes
The best app I found is Dual SIM Selector https://play.google.com/store/apps/details?id=net.pixelrush.dualsimselector I have work and personal contacts separated exactly as you (Outlook and Gmail), and this app works perfectly.
There is this program https://play.google.com/store/apps/details?id=net.pixelrush.dualsimselector There are some reports with this bug in playmarket reports. I contacted the developer, but he made no visible attempts to correct the situation. I can not create a ticket for the 'Weekly / Nightly' tracker, only for REGRESSION tracker. But it's not a regression.
Worked the dual-sim life for over a year with my ZTE Axon 7, and then on my Nokia 6 (dropped the Axon in Vietnam, bought a replacement while over there).
On most current dual-SIM phones, whichever SIM you've marked as your "data" SIM has the 4G turned on, because 4G is a data-only protocol; "Voice over LTE(4G)" calls have only recently been enabled (noticed call quality has improved?), otherwise, all calls back down to 3G anyway.
There's no technical reason why there can't be a dual-4G dual-SIM phone; there's just no real market demand to have 2x 4G radios.
When you're on the phone and you receive a call on the other SIM, it just sends it to voicemail.
I had Voda (personal number) as my primary sim, and Optus (work number) as my secondary sim. I was using my Voda sim as my data sim for the majority of the time, but when Optus started offering unmetered spotify streaming I trialled switching the SIMs for a few weeks and noticed markedly shittier reception and speed across the board (CBD, suburbs, shopping centres and underground carparks).
No discernable difference between the two areals as far as I could tell (though that could entirely depend on the quality of the phone).
Apps that rely on a phone number ask you to put one in and send you a confirmation text; it doesn't matter which one you use because you'll receive the text. If you want to use two accounts, you'll have to use Android's "Users" feature (which is a PITA for frequent use).
There is an app called Dual Sim Selector that might be really handy for you. The way I organised it was that I kept my personal contacts in my personal Google account, and my work contacts in my work Exchange/Email account; in this app you can set it to automatically choose which SIM to dial out when it matches a contact from either account, otherwise to ask you.
SMS SIM selection is still manual, never found a solution for that. I really wanted an SMS app that had separate tabs for each SIM, but I couldn't find anything; your SMS inbox will just be mixed.
Anything that uses Google Assistant (Android Auto included) does not understand dual SIM phones and will use your primary SIM for everything, including replies to text messages regardless of which SIM they were received on.
Say goodbye to work-life balance; it's a very quick way to blur the demarkation lines between work and personal life if that's what you're doing with it.
Get the Nokia 8. It's a solid phone, stock Android, updated quickly and frequently; no gimmicky bullshit and sideloading the Pixel camera app makes all your photos look great.