Let me know if this is a good deal and if I am not factoring anything.

Any bank will look at many factors but for a residential loan (which you would need for a building up to 4 units), it mainly comes down to your DTI (debt to income) ratio.

This saves me and staff time from driving multiple times to properties, it prevents wasting time in the event of a no-show, and I found it creates a sense of urgency in potential tenants as when they come they see other folks looking at the unit. 

What is a key factor that will determine a deal going through? 

All of the factors you decide on determine what you will be drawn towards.Person to person, we all have different levels of risk aversion, time, etc. and that is going to determine a lot of things for you.

Having them drive out 30 minutes to look at a retaining wall to turn around is not on the "fun list". 

All the factors that play in are extremely complex.

Rental income is a BIG factor in analyzing deals so I wanted to ask the community for any tips and advice before moving on.

I look at my return on the investment only factoring the interest portion of the mortgage payment but use the cash flow side to get a better idea on how the property will work with financing and scalability.  

Factor your repairs into your price and go for it.