When (if) I choose to move on to something else, I will continue using a property manager rather than do it myself.

All without using a penny of my own cash.

Purchase with a Fix & Flip loan, then cash out refi using a DSCR loan on the exit.

I recently started using a new painter and I'm wondering if he is over-estimating material on purpose or if I'm just being stingy lol. 

A cash out refi using a DSCR loan could work well for this.

Are you using a PM? 

I've been using a local bank and local builder for my projects in Florida then a refi into a DSCR after construction to get back as much capital as possible. 

I watch Brandon Mulrenin for his cold calling content, just for knowledge, however when I obtain my license I anticipate using a different approach to his when it comes to personality and tone. 

When first starting out using a Buy and Hold strategy and with limited capital, do you think it's better to purchase a bunch of lower priced properties in lower quality / depressed areas or spend a little bit more but have less quantity or rentals (but presumably higher quality tenants) for properties in an area that is well known for being a "good" area?

Your family might benefit from buying a 2-4 unit property with 5% down using a conventional loan.