I also rented nearby and could be at the property frequently. 

You should have a pretty decent idea of what homes are worth/what places are renting for and you can make an educated decision from there.

If you find yourself saying "I am new to real estate", then you do need some time to educate yourself (BiggerPockets is great for that) and plan your first investment carefully before jumping in.Remember, buying a traditional rental is one of many different ways you can enter REI world.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

My gf wants to pivot and rent the house while we live in the condo, but my brother is not educated and is afraid of being a landlord.

Specifically, I'm wondering about the best first steps for education and whether getting a real estate license would be beneficial.

https://www.biggerpockets.com/...12 Frequently Asked Questions (And Answers) About DSCR Loanshttps://www.biggerpockets.com/...8 More Commonly Asked Questions and Answers to DSCR Loanshttps://www.biggerpockets.com/blog/eight-questions-and-answe...What Documents Do You Need for a DSCR Loan?

So, for those who frequently hire contractors (good ones), how do you find good contractors?

We are looking at what's next and want to absorb all the information we can to make the most educated decision on our moves.

I highly recommend reading the BP books for self-education and house hacking a 2-4 unit property for your first deal.