I find that the market rents in Cleveland are pretty decent and compared to the state that I live in currently all the 3 major cities in Ohio do have a low barrier to entry.

Example: Tenant experiences a loss due to some house issue.

Just finished my major in Business Management and am receiving my Management and Supervision certificate this summer.I've been studying real estate for a few years now, have watched tons of videos, calculated and ran numbers on numerous properties and listings, and talked with many lenders and real estate agents, but because I don't have anyone in my circle that's well-experienced in REI's I've hesitated to pull the trigger on anything.I'm looking to fix and flip, BRRR, LTR, MTR, STR, or multi-family.

Usually if there is a plumbing or electric issue, it falls on the tenants.  

Banks/Lenders use a theory that if an investor encounters a loss be it in income, death, divorce, major sickness, or any other set back they are more likely to let their 2nd lien positions go in default before a 1st lien.Reason why I say this is although you have a great rate on the first mortgage you need to let it go and do a "Cash out refinance".

So my conundrum is do i just keep renting to a new tenant and deal with the maintenance expenses as they pop up, or do i try to get out now before a major expense pops up and just take the little bit of profit (less the capital gains tax)?

We sold, again management issues and we were out of state.

I'm planning to purchase the SFR with a conventional mortgage, but my mortgage broker and underwriter are telling me this will create a lot of issues both legally and with the bank once I demolish the property and try to subdivide; since the mortgage is for the full property. 

You might laugh but being a new person in very new situation creates these kind of issues.

For example, when pha slaps you with a surprise inspection cause their system "forgot" to send a letter and then issues a 24 hr repair notice cause one outlet in the house does not work but they send that notice an hour before they come to reinspect lol, a $7k course is not going to have prepared you how to get an electrician the same day.