@Robert Gibbs welcome, and good luck on your investing journey.My two cents:  a house hack (which can be a single fam or small multifam property) is the best way to start off--and is a far better strategy for a beginner than an OOS property.A good house hack will simultaneously lower your living expenses while increasing your income (the fundamental recipe for building wealth), it will teach you many of the essential skills you'll need to succeed in REI (like due diligence, tenant screening, property management, etc.), and--importantly--it's MUCH simpler and easier than other strategies like OOS investing (which tends to have a lot more risk and a much steeper learning curve).  

Posts here say CF is sometimes sacrificed for appreciation, while others say go for both simultaneously.

@Ethan Waltersjust curious, why do you feel you cannot pursue both simultaneously?

How would someone transition to getting the next while simultaneously making to former house into an investment property.

As time goes on and rates drop back down, prices will likely rise simultaneously.

I would simultaneously put pressure on the other Landlord that allowing this guy to stay is costing you money and you may decide to come after him for it.

Due to the volume I wish to offer on, it is not feasible to go view every property.Am I able to structure simultaneous offers on multiple properties in a way that my realtor will be willing to execute, and will also allow me to inspect prior to a deal being done.

I fully realize that it takes 10 seconds while simultaneously understanding I just about never do it with my own smart thermostats over the last 9 years. :)

It takes an avoided passive expense (avoid property manager), creates a passive expense (property manager) and simultaneously creates an active income (self-manager LLC). 

I did another, better one, simultaneously with one of my partners that I am training.