Which cities and areas do you think have the greatest potential for appreciation?

If you can not find coverage with the agencies you have contacted, PM me and I will let you know the companies that we use that might do it.Because of your making payments to the owners potentially, I would look into commercial crime coverage and cyber liability. 

Builders do this a lot to add extra potential sleeping area without having more bedrooms than septic is rated for.I have seen people put beds in the loft after closing or even close in this area to make an unofficial bedroom.Just be clear in your pictures and description and you should be fine either way.

Instead, the income (or potential income) of the property would be used for qualification.

Investment needs to pay attention to the quality and potential of the real estate.

At least this next potential home is only a single story so I cant fall as far. 

You would want to know if anything was ever built on the land (maybe a house burned down) because if there was a house then you would have potentially buried septic or oil.Buying and holding a lot for the future with topographical issues is only worth it if the price is negligible IMO.

This could be a great way to get started as you'll be at the property everyday and by living in the property not only will you be there firsthand to oversee the work being done, but you may also find new potential issues while living there.If you're looking to do this, I'd recommend a 203k loan to purchase the property and get some rehab funds. you'll just need to live in the property for a year before being able to lease it out to a tenant.

Consider what questions the potential mentor may ask and how you would answer.

Look for properties with low taxes, separate utilities, strong demand, and potential for rent increases.