You should know the target investment area well enough to quickly recognize actual deals versus those that are not going to be profitable.You should then have a team in place that can quickly validate the condition of the property and give a decently accurate estimate of repairs. 

How much work do you think 4 buildings are versus one?

It does sound like there is a categorical difference in that evaluation versus staying relevant by keeping up-to-date with "must-haves" that are common among the top performers in your given market.

If you have several properties versus one they are more likely to work with you.You can sell one off to cure another loan.

Is this a good term versus what the bank offers? 

Hopefully you will have a starting salary in the form of a W2 income versus a 1099 income.

Also, at what point do we consider this a rental versus a second home?

That can make all the difference in negative cash flow versus a 5-10% return. 

A more important question is how much is your PITI payment versus your $1100 a month rent payment (assuming you're going to rent the property) since you want cash flow.  

These items will eat into your actual returns versus proforma.