In that case, you may have trouble getting the property for your offer price because the current homeowner would have a lot of incentive to get a higher price by either replacing the roof themselves before selling or offering a credit at closing to an owner-occupant buyer willing to replace the roof.

Even in the worse case scenario of a 0 occupancy I could carry the full mortgage.I know this is a pretty big leap from nothing to home owner. 

I have some background on her occupation in the service industry.

For example, a penthouse suite in Chicago renting for $4k -$6k a month, needing $20,000 in furnishings, but seems to get no less than 50% occupancy at $1,000 a night...sure, it's a lot more upfront and quite a commitment to rent such a place, but the revenue is so much larger...

Might have to build near cities that have higher building occupancy percentages. 

Has anyone had success following the traditional idea of occupant owned/lot rent system but with individual lots in different locations?

Don't pay a builder in full until your have a Certificate of Occupancy.

They can limit the # of rentals, the type of pets, if owner occupants or renters can have pets, where you park, flag poles, types of landscaping, amount of landscaping, if you can park a boat or an RV and for how long, what size of house you build, how fast you have to build it, the amount of brick you have on it, what types of flags you can fly...and on and on and on.   

I have some background on her occupation in the service industry.

You can evict all "unnamed occupants."