Main question is if I do #4, is #1 redundant or still beneficial/necessary? 

I would recommend a triple net lease (NNN) where the tenant is responsible for paying additional fees - the property tax, all maintenance (including or excluding the roof - (your choice) and insurance on the property.

But if there is a way that I can't put all my eggs in one basket with a market that has not a very good reputation with forums and sites that ranks Cleveland as a city of last choice, why not ask for opinions of people who know their markets well, their advantages and disadvantages?

I would NOT provide a lawnmower, even though it came free - since this creates a liability for you.I would give the tenant a choice:  (a)  they are responsible for their own lawn care / snow removal, or (b) the landlord will take on that responsibility with an additional monthly charge of X. 

If you can do a land contract and keep title that would be more beneficial to seller

The choice is ultimately up to you! 

Neither one is the wrong choice.  

I have heard it being done and can be beneficial to both sides but that's just me. 

Those who care most for you will often give advice which is more protective, as they care about you, instead of beneficial to your financial future or goals.As far as, are you ready, I'd say you are more then ready.

You basically have two choices right now, you can put more money down or have a higher monthly payment.