Things like what market it’s in, what condition is the property in, what the rents are and what the market rents are, and most importantly what are your goals.

All depends on your long-term goals. 

I'm currently reading "The Book on Rental Property Investing" and have a goal to start my investing career by purchasing a small multifamily to house hack by the end of 2019.Any advice on either topic is greatly appreciated!

Find the managers who best align with your goals, they all have their niche's.

I don't care for wholesaling and it's not my ultimate goal but seems to be a necessity at the moment (no money not much credit.)

If it is your primary residence, there may be programs available where you could get in with only a few percent down.As Dan Barli stated, your goals certainly come into play.

This is a really broad question, but you should really question what are your goals. 

I am in full agreement that a positive cash flow is a very important goal, due to the fact it insulates you from gambling on appreciation, equity, and rent increases. 

What are your real estate goals?

I've been wondering do I find a less thorough but competent Mortgage Broker who works faster because he requires less documentation.