In this arrangement, the buyer signs a contract where one of the clauses specifically says that he assumes responsibility for the loan which remains under the seller's name.

Assuming you purchased in your IRA for cash as most do, then there's nothing to deduct or depreciate because the income is non-taxable inside the IRA already.

In our experience, the #1 mistake landlords make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.

I am assuming short-term rentals would be legal in the municipality.

Assuming I get an appraisal of $500K, I have ~$110k (75% of appraised value minus the loan) I could tap into for equity for a HELOC.Question: What is the process for getting a HELOC?

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

You are only adding complications and costs with the LLC with no upside  This is all assuming there’s been almost zero appreciation and you shouldn’t sell tax free while you have the chance. 

Send it to every address they give you including the current rental assuming it will be forwarded to the address they gave the post office.

That calculation also assumed $0 renovation and $0 furnishings, which won't be the case. 

Most people assume that house hacking means living in a 2 bedroom 1 bath duplex.