If you would clean up the mess and walk away then you need far less. 

After signing hundreds of properties into the top 2 vacation rental companies in the US, I can walk through a home in 10 minutes and let you know it's highest and best use as a STR. 

When a property meets my criteria I need to be ready to walk the property and submit an offer.

I have a trustworthy friend who is down to walk the path of real estate investment with me. 

@ChristianWeber I see you have 3 choices: 1-Accept as is and eat it(not recommended)2-Walk away and learn to spot some of the issues before you pay for an inspection. 3-Ask for cash back at closing to cover things in report, start around $15k-$17k looking at your numbers.

My first idea was to buy something small and do short-term rentals for the days I'm not using it.I've also considered buying a tri or quad-plex or even something a little larger around 5-12 units and keeping one for myself.My other option is to buy something with a walk-out basement and rent the other two levels out. 

My goal is to accumulate cash flow over these next 13-14 years, which I would essentially consider "off-limits" until the day I walk off my last ship. 

If the appraiser absolutely can't make it out in time, you can renegotiate a few more days, or the seller can walk, but at least you got to that point. 

My question is this 2 of the bedrooms have a door separating them commonly known as a walk thru bedroom.

I don’t advance or do favors because then next time it’s little more money and little further in advance then More and more and before you know it this guy owes you a few grand and walks off to go take advantage of someone else.