But as reality sets in, I probably can't swing both financially at the same time. 

Now we know our all in is 2,100,000 and our yearly gross potential is 842,400.

Not a whole lot you would need to ask the agent, You need to do your homework on the property, search your own comps, know your costs on the renovation like the back of you hand, and learn the areas your intending on flipping in, ie recent home sales, crime etc.

Hi Guys,Brand new landlord here and was hoping the BP family could help.I had some tenants move in and signed a lease indicating no pets and making no meantion of any emotional support animal.One month after move in, I drove to the property and they had a dog.  

I was disappointed to hear this since multi-units under $250K are in the least desirable neighborhoods, where I would not like to live in.

Yeesh.The building is old but what condition is it in?

This is a good reason why you do a walk thru with the tenant and have them sign a document stating the condition of the place upon moving in.

I check and analyse properties every evening after my current day-job and early morning before I go in. 

Cleveland is a great city to invest in.

Once you're in I wouldn't ask for his mentorship but instead bring very specific questions to him to get his opinion.