Job market- there will always be a job for you somewhere. Like most specialties, you may have to sacrifice one thing for another- ie take a lower salary to work in a saturated, desirable city.
Salary- What do you want to do and where do you want to be? As a proceduralist you're not going to starve, no matter what. But my friends who had to build up their patient base worked harder for less or the same than I did joining an academic practice. Eventually, they passed me - the ones in saturated areas took longer than the ones who went to places that desperately needed docs. I've seen starting offers for graduating residents range from $160s to $300s depending on a variety of factors. That can go up as you become established in practice.
Mid-level encroachment- A non-issue. Yes, there are CNMs and WHNPs and PAs, but I've never come across any of them clamoring to increase their scope of practice beyond clinic or (for CNMs) the uncomplicated delivery room. I have plenty of colleagues who work with mid-levels to increase their own practice's productivity.
Malpractice- Having only worked for a state university and the federal government, I'm not the best person to ask. But $40K a year sounds right from what I've heard- also in a doctor-friendly state.
Residency- Four long, hard years. Because of all the different subspecialty and procedure exposure you have to get, there's never really a point where you've "gotten" everything and can coast. Additionally, if you have your eyes on a specific subspecialty, it might be very tough to grind out the four years of general OB/GYN. I've seen future MFMs who were miserable for every single GYN rotation, and future oncologists who wanted to die every time they had to cover the labor floor. Not a great way to spend four years, but it is self-limited and got them to their goals so I guess it was worth it for them. Some are advocating for differentiation via residency tracks, since it is tough to squeeze in the entire breadth of the field to a meaningful level of experience in four years. While this may well happen, it won't be quickly- it would mean a retooling of not just residency but board certification.