What sort of discount should one expect on a house like this compared to "regular" lot with all other things being equal? 

Basically this is stating that what the market rents are need to equal the mortgage payment or exceed.

If you buy a property with a building on it, your dollars spent on improvements must be equal to the value of the structure on the land. 

When you are looking for cash flow, the total cost of the property (buy, interest, rehab, etc...) isn't equal to the total cost to you.

I know these may not be a every single property decision type of thing but they could be tools put to use lower payments equal more cash flow so you could make somthing work that way.How do you go about finding these loans  vs 30 year loans.

Divide that by 12 months equals $63 / month. 

Even if he is subsidizing it $300 a month, that extra $100K equals 27 years worth of $300 payments! 

It will likely only go up if there is a city wide reval, but you can figure out easily by using your purchase price, the equalization ratio and rate for worst case scenario increase.

You are equally free to succeed wildly or fail just as well. 

I became a married man just two weeks ago to an equally motivated and supporting wife.