However, I am optimistic that when I am willing to put good chunk of my money on the line, there will be investors/lenders who'd be willing to work with me to realize a viable project.

Then repeating this for the down months.I am very optimistic but I have no experience in real estate flipping, but I do want to venture in.

The plan is good even though as the others have pointed out your numbers are extremely optimistic.

Overall the economic future of the city is not optimistic, but believe it or not, the rental market should remain relatively consistent .  

A few of these numbers I feel are pretty optimistic, so I'll spend some more time investigating to get them to what are hopefully closer values.Someone mentioned not being able to get a 30 year amortized loan. 

Very frugal and hardworking kid, but too much of an optimist!

That sounds amazingly optimistic, not to mention he needs permits, they will need to inspect the hvac, electrical, insulation and framing before he closes the room in.

Being young and highly optimistic is understandable but as long as he calculates the downside if it does not work out in his favor he should be fine. 

I always tell people who ask this question never to be overly optimistic when deciding if the house is a good rehab.

Since I began this they topic I have spoken with them several times and they seem much more optimistic.