If you're selling to flipper and the contractor isn't part of that, not sure it will be possible to get a reliable person. 

Of the two options you mentioned, I personally love house hacking.

Consulting with financial and legal experts ensures that both the sale and the subsequent purchase align with legal requirements and your personal financial goals.

Once you feel you've built a strong team with your first property and have solid systems in place, I would then start buying more aggressively and taking on bigger projects.I suggest reading this BP article on the core 4.https://www.biggerpockets.com/blog/core-four-real-estate-team

Any other suggestions or advice is very appreciated and feel free to message me directly.

A person with a reasonable full time job is typically a more responsible adult and has to act in a professional manner for their job. 

You can program from remote location, key cards have to be done in person.

They claim it will boost property value.It might, but I feel like that is should I should have known about prior to purchase and I'm also unsure how the city can do this with out permission or paying for it.

@Bruce Woodruff: Sounds like a personal problem.

This is tougher to explain in detail so if you have any questions feel free to reach out I enjoy helping and talking REI!