I have a mentor i've been shadowing for about a year now as well.

You need two years of steady income before you can qualify for a loan.

Feel free to browse my old cringe posts as proof lol.

Where do you want to be in life in 3-5 years?

The market has gotten much higher than in recent years. 

Is anyone out there willing to be boots on the ground in Cleveland particularly old Brooklyn to check out the condition of a property?

The building is 100 years old, but solid with regular maintenance and updates.

There is an old saying that might apply here.

It would pi$$ me off to no end if a 19 year old came to talk to me with a binder telling me how good of a deal I am getting by seeing a 36% rent increase.

Most inspections are exterior only so insurance is going off of insured/agent application and any visual cues such as an outdated electrical meter.Also, while it's been difficult to insure these things for many years now it's gotten tighter over the last 5 years in this hard market.