Say it takes you 12 months to get that person out before you can even lift a finger to do any work, and say that they leave the place completely destroyed.

Thankfully, my wife is 100% on board and she's even learning about house hacking on her own.

But you made a good suggestion, and I agree it'll be messy for me to determine what's tenant damage and what's not (even with the move-in report). 

If it is a disregarded entity LLC you're not even changing the tax payer and could do it immediately. 

Do you even know how to operate in a customer service oriented business?

Even if newer buildings can't price rents as low as yours, they might offer amenities or modern designs that attract potential tenants.Local Economic Factors: Consider local employment rates, major employers relocating, or any changes in the local economy that might impact rental demand.2.

LLC's can sometimes complicate things, just open a bank account for your rentals and use a program like quickbooks to do and manage your books. you could even hire someone for around $100/mo to do this for you as well

Even if it is not a requirement to have a high credit score for approval most asset-based lenders will use the credit score to determine your rates and terms based on your risk factor.

First of all, does this even sound like a good investment strategy (going into negative cash flow)?

So even if the ARV would be $240,000 and could rent it out for $2,000, I would leave money on the table?