I'm moving to Cleveland and looking for a duplex for my first house (graduated college a week ago) I have a family member here who owns a few houses and has retired off of their cashflow.

I am currently a Junior in college and looking to purchase my first property as soon as possible but also considering the value of waiting until I am settled into my first job out of college.

My philosophy with contractors (in the past) has been - "hire the right people and stay out of their way".I need an honest, reliable, cost-conscious GC who can pull permits, demo and knock this "fix n flip" out in 3-4 months.  

I currently go to college for my Network System Technology degree.

Ontario poses a challenge as rents can't be increased to market... case in point, the ON gov just announced a 1.2% permitted increase on rents next year... not even keeping pace with inflation.  

I am a 22 year old who is about to start his last semester of college, then will finally graduate.

I'm pretty sure you need to occupy the property to be able to get an STR permit. 

@Jonathan BellI was lucky to meet mine in college, and it's been a blessing.

Part of the reason I’m looking into this is for speed over traditional stick built homes :)I do a lot of planning and scheduling for design, project management, and permitting for Connect Homes, a modular prefab home company.  

It is encroaching past your frontage which if I processed a permit to install the service the City wouldn't normally allow, but as an existing condition there isn't any specific issue allowing it to remain.Generally it's not likely that any of your proposed improvements would be immediately adjacent to that PL anyway, so leaving it in place likely presents almost no impact to your proposed development.