At an extremely basic level you should understand and be able to articulate: investment criteria, underwriting best practices, property management, exit strategy, securities law, macro- and micro-economics among other topics.The more comfortable you become you mitigate the risk of making a life altering decision. 

I can't articulate how much I enjoy talking real estate with other serious investors.

And I'll do my best to answer your questions as articulately as possible. (1) Yes, the cash out refi will definitely pay a role in my future decisions on when to time the refinance.

We are missing something not articulated in your question

How do I articulate my goals (wholesaling) so that the Realtor is open to helping me.

Instead you can offer a lower purchase price, articulating the business risk you are taking on based on the dynamics.My sense is this is a tired landlord situation, so any way you can make the deal more "clean" (e.g. cash offer, no contingencies) might increase your chances. 

It may not help but I think you have articulated most of the considerations quite well; Flexibility vs.

It is equally important to clearly articulate expectations regarding rent payments and the consequences of non-payment, providing tenants with a clear understanding of their responsibilities while also ensuring that landlords can maintain a stable and reliable income.

@Joel Florek It's extremely refreshing to see somebody else on here who is not only young, but able to articulate their ideas and come off as prepared, knowledgeable and intelligent.

A good sponsor should be able to articulate to LP's their competitive edge.