Insurance not covering it would be the least of your problems.

For example, more downpayment means less interest rate regardless or whatever loan.I am trying to see what sort of action I can take right now so I can plan detailed and measured steps to my goal.

The planning process can take a very long time!

I was planning on searching here today to see if I can find any meetups in our area.

Network with experienced investors, choose a real estate strategy, research markets with job and population growth, learn financing options, familiarize yourself with property management, develop a long-term plan, and leverage your stock experience to evaluate markets and trends.Good luck!

I used to work in Planning & Zoning. 

Raleigh specifically has introduced “Fast-Track Plans” designed to streamline permitting to build ADUs faster and more cost-effectively.

If you aren't planning on ducting, then mini splits can be the way to go.

Add another $300 or so for taxes and insurance and you're at $2465 PITI. 

I recently purchased a 2 unit property as owner occupied with one unit already rented out. 3 months after closing, I was laid off due to a restructure at my company, so I decided to rent out the other unit my girlfriend and I planned to live in.