How much would you increase the rent by?

How it holds me back, is that when you hold a license, you are, or at least from a moral compass, should be held to a higher standard and follow the ethics of a real estate licensee. 

By day I work in the oil and gas sector as an accountant, but I'm looking to increase my knowledge related to real estate and hopefully invest in some buy and hold multi-family units for some additional long-term cash flow.

This would allow me to increase my portfolio by a home every few years if I put my rental income and additional income into more real-estate. 

I followed up and mentioned that I wanted to increase rent about $50 (~3%) minimum.

Just talk to some local lenders about what their refinancing policies are.As I see it, if you want to be able to pull all ypur money out when refinancing you either have to buy below appraisal value, do renovations that increase the appraisal value more than the reno cost, or both.You can buy properties in good condition that cash flow well, but you probably won't be able to pull all your money back out unless you are buying them well below market price. 

And if not, is it possible or beneficial to convert the house into a commercial property so I could raise the NOI and increase it’s overall value?

I would suggest buying replacement policies in the beginning and simply increasing the deductible to 2500, 5k and then 10k as you grow and can take on more risk.

She should also be making additional payments toward her student loan debt to you when she can afford it or when her income increases.

Each property has it's own LLC and bank account for which rents are deposited and expenses paid, but if one does not extract money from these business accounts, how can you keep increasing personal debt without increasing personal income?