I think you’r paying the price for shady wholesalers. 

I would anticipate roughly 20-40k depending on how deep you have to go.

Hey Ryan, I know there are some folks that provide this service but I'm not sure exactly how it works and how much trust is involved.If it's any consolation, I wouldn't sweat it too much.

As I begin this new journey, I would like to ask some questions that I hope more experienced landlords and investors can answer.

Pretty solid points here, I would also like to add refinancing with a non-traditional DSCR based loan can assist with getting access to cash quickly as there are many lenders that have a lower seasoning requirement. 

Am I missing something here?

As I often tell my students, “Refinancing is a powerful tool in your real estate investment arsenal.”Investing in Nicer Assets.

I think you'll have to sign an affidavit stating you plan to occupy it. 

I have a feeling things will work out a lot better.

Hello,I don't know what you mean by lender.