Than be smart, site back and listen, take it all in, be a good student. 

What would be my best route to take if we need additional finances?

Coaching is a great option if you're looking to take action quickly.

The units are all currently occupied right now, so we won't have to worry about the buyer's market right now haha.With the cash flow I will receive, it will be enough to take care of property taxes, insurance, and enough to save up for any emergiences with the unit that I will need to take care of, so no need to worry, I got you :)!

Here are the details:Purchase Price: $300KDown payment if taking mortgage: 10%Available cash on hand: $40KEquity in Primary Residence: $700K - $1MSecond Home will need $10K initial investment to freshen up for personal and STR use.Assume equal rates for each product? 

Permitting does take quite some time but you should factor this into your underwriting.

You can always take extra courses or certifications later to level up your skills.

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

It’s exciting to hear you’re looking to scale up into larger multifamily investments—financial independence is a fantastic goal, and it sounds like you’re taking the right steps to get there.It’s great that you’re already focused on assembling a team and diving into market analysis.

That would take 2.5 years just to break even.