I don't think its as easy as people make it out to be. 

This can also be triggered if they have kids or what they perceive to be valuables in the home that have not been secured.It can also relate to how you conduct the inspection.

I'll check around with some lenders to see what they share about their comfort with the timeline - whether HELOC or not.  

You would have a smaller discount, but would have little to no out of pocket annually.

Is this a good way to get into real estate investing?

Going through my real estate journey I have learned a lot, I am 24, a veteran and a graduate from Temple University,I started with aspirations of investing on a property and making a quick flip.My problem lied with fear of failing, my capital and my savings.I decided I wanted to learn the real estate market and know the ins and outs before I would make a bold choice on buying my first real estate home.

Feel free to reach out if you still have questions.

This thread is very informative and helpful.

You really should talk to a CPA and show them the details of this property and how much depreciation has already been taken on this property. 

Highly recommend you looking into a checkbook IRA instead of cashing out.Sure you can take out the principle since you’ve already paid taxes on it but this money is supposed to be for your retirement and in a Roth your real estate can grow tax free, though check with a CPA to see if STR will trigger UBIT in an IRA.