But as a first-time buyer, there are so many things in the process I am just not familiar with, including how to structure the offer, being able to view listings on Costar, doing due diligence, etc.

All of us who have done this long enough have had our 'plans' go awry on different investments from time to time. 

And still have plenty of time to get your old property sold with all of the due diligence tick points you'll have with a MF.

Far too many investors spend way too much time, money, and energy creating LLCs or other complexities that serve no purpose.An LLC is useful for two things: anonymity and legal protection.

He does this for mine for a low flat monthly fee and he really helps fill up the weekdays/off seasons and optimize booking revenue during the peak times.

I've been in lending for over 5 years now, but this is the first time I now have to file an MCR through the NMLS. 

I work in commercial property development, but this would be my first time developing anything myself and developing anything residential.

Have a good team solves a lot of issues in real estate (as does time)

Quote from @Calvin Drake: I've found that some of the zipcodes on the northside (32208, 32209, 32206) have adequate opportunities to meet the 1% rule; however, with some deeper looking you most definitely can find properties elsewhere in Jacksonville that may not require as intensive of management as Ken mentioned.Can you explain what you mean by “deeper looking” other than looking at public listings or going into wholesale which I don’t have time for? 

Ideally something that is on web/app that'll allow me to keep track of different items come tax time.