The reason sellers cannot sell these properties through the traditional market is often due to certain issues, and 98% of the time, these issues are not beneficial to you as a buyer.

Unfortunately most lack the balance sheet to obtain favorable financing, can't afford to put any skin in the game and fail to make a compelling reason for why the investment makes sense or to justify the structure they are seeking.

This is one of the biggest insulation issues second only to the attic.

Why are you entering a hospitality business to automate your (im)personal responses when guests have an issue?

They are paying for some repairs now after I've had several issues and a brand new tenant moved out, but I'm still paying a mortgage without any rent coming in during those months. 

Keep in mind that I am selling them as affordable fixer uppers and usually only address any health, safety, and functionality issues.

Lender A misses this or doesn't have this knowledge and then tells you a week before closing that your rate is changing because the program they quoted wont work once the issue is caught. 

The interior was outdated, the landscaping was overgrown, and several deferred maintenance issues were apparent.

You are micro-analyzing the minutia of each offering, but that's not really the issue.

I've been teetering around the idea of house hacking once I am done with college, but a big issue I have come across when speaking to a mortgage broker is the fact that I need to prove 2x of the mortgage in monthly income.