There is so much and you have an in-house expert at hand, but I'd say one thing is to visit the Domaining.com site daily or at least regularly to see the domain headlines of the various domain blogs. To see what is trending and what is selling. Also check DNJournal.com for the weekly domain sales report to see what sells, and what extensions are popular.
Don't extend yourself financially, especially as we may now be going into a recession or slowdown. That said, from being in domains 22 years I can say that domain sales kept happening through every previous slowdown. Probably because the internet and tech was still in growth phase, and a business needs a domain for a website. So the tech trend kind of made up for the slowdown in the general economy. And that effect might still be in play for more years ahead.
Look at the renewal price for domains you buy. Some extensions have $40+ renewals so it's harder to maintain over time if you aren't selling and have a lot of those. The .io extension is pricey for example. .com and .ca are good in comparison for renewal rates. As you grow your portfolio keep in mind you are increasing your annual costs if you plan to renew them all.
Back in 2000 I 'should have' focused more on quality than quantity. Back then you could have bought names in the aftermarket for 100's or low xxxx that are now easily xx,xxx or even xxx,xxx. Also, if you have a smaller portfolio of high quality names, that is less annual renewal fees than a large portfolio of mediocre to decent domains.
It is always a balance about what to keep and what to drop, balancing costs vs sales, for everyone. And domain quality is so subjective, you never know what will sell or not sell. For example, I still haven't gotten over how popular .xyz has become and all the high sales it's had, since I remember when it first came out and didn't get much respect for years. Anyone could have built up a good portfolio of one word .xyz back then that would be very valuable in today's market.