Are they assessing a proper amount for the monthly upkeep?

You may not get landlording experience but you'll get maintenance, financing, and paperwork experience.I think the discussion points in your head and with them are around what kind of improvements they would need or desire (if you have to make it elderly accessible that could be a selling point for the next tenants, but what if they want something that will cause you more upkeep in the future?)

If it can give more weight to recent contacts in searches would be great too.  

In Cleveland, many landlords do not provide sufficient property upkeep so an investor has to be prepared when the "Must-Do" repairs arrive and tenants vacate. 

A good mentor is worth their weight in gold, at least mine was.

Roof; Furnace; Basement upkeep)?

I bought a car for $2,000 dollars F+C in college and over 3 years I put over $8,000 in upkeep in to it but that doesn't make it worth $10K.As for the lease option structure, it looks like you understand it pretty well.

Just a preference and I don't think it would be difficult to upkeep, but that depends on the tenants and if they charge extra to mow and trim.  

If you are trying to wholesale it, don't. 95% chance you'll just end up keeping their home off the market fit 60-90 days, so they can't sell to a real buyer, then the deals falls apart because you find a buyer, your double close doesn't work (no assignments allowed), etc, etc.

student loan debt is highest weighted hit when trying to get a loanif money is no object to you, get a house in west u and youll prob preserve your capital