*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

Becoming a real estate agent is a good idea to gain experience, but you could also explore property management, wholesaling, or working with an investor to build your network. 

1) If you've got guys willing to front all the money while you gain experience and make some money then that's a no brainer.

Most important thing is gaining enough knowledge to be able to purchase properties that's going to add value to the next few years of my life and my kids 

Even then, the IRS may scrutinize the transaction if it appears the intent was to immediately convert the property into a personal residence.Additionally, if you eventually sell the property after converting it to a primary residence, you may qualify for partial benefits under the Section 121 exclusion for primary residence gains.

Day traders are not exempt unless they elect mark-to-market (MTM) accounting, which eliminates wash sale tracking but taxes gains as ordinary income.To manage taxes, track trades closely, avoid overlapping purchases, or consider MTM election if trading actively.

And, the longer you wait to act, the longer the squatter stays - and even gains some legal protections to stay while your waiting on a slow court system to act on an eviction. 

They also are thinking of getting a different PM to manage it after they can gain back control but would like advice on doing so.

It takes time and patience, but the long-term benefits are well worth it.I’ve personally gained invaluable knowledge, listings, and deals from friendships I’ve built over the years.The more people you engage with, the faster you’ll achieve your goals!

Like you, I’m diving into books and podcasts, but I also believe there’s immense value in learning alongside others and gaining hands-on experience.I’m in the process of connecting with like-minded individuals to create a community of new investors who are eager to learn, share knowledge, and even collaborate on deals.