I supply paper products, coffee, hand soap and cleaning products.

The owner also provided daily cleaning services, access to dedicated Wi-Fi, access to beach and recreational equipment, and prepaid ride-share vouchers between the rental property and the nearest business district.

Signing a fresh lease keeps things "clean" in that if you need to prove something later on you don't need to examine several documents and consider the changes in the order they were made.

She even said how clean it was when she first viewed it. 

If I get one then I’ll need to have my title cleaned after with a quiet title process anyway.

I've begun volunteering with Habitat for Humanity to gain more confidence in DIY improvements. 

I agree that it's harder to manage by the room logistically (roommate dynamics, common area cleaning, etc) but it is allowed. 

Sell the land as a first step in cleaning up your balance sheet.2.

Believe you will need to refinance to keep this clean.  

I have been a landlord and investor for over a decade AND also work as a senior/regional property manager so I feel like I see both sides and have some good insight on this- manage yourself if you have the time and fortitude to do so, you will make mistakes but it will pay off, get a real estate license (not hard to do plus you can sell and buy properties and get commission) and know the laws, be willing to do the research, NO ONE IS GOING CARE AS MUCH ABOUT YOUR PROPERTY AS YOU- that being said, not everyone wants to has the time ect or headache or likes asking for rent…FIND A MANAGER THAT ALSO IS A LANDLORD INVESTOR, I can’t tell you how many property managers I’ve tried training and that failed at our company because they just don’t get it from an owner or investor side, like “no tenant we aren’t going to come replace your stove again, no we aren’t going to clean your bathroom cause you didn’t , ability to analyze when to do maintenance and not, ability to explain to tenant owners POV, I tell every owner I am not telling you anything I haven’t done or I’d do my self, a lot of property managers are blue colar type workers and have never invested in their life and just done get it, 4 out of 5 property managers fail at my company because of this especially for single family homes, find a PM with speciality in SFH for your area, for example, a PM in Birmingham MI (upscale area) will fail in Detroit or lower end markets (but that’s were the best ROIs are)