Best time to approach a bank is when they sell out to another bank, change of management or when a new one is going to open.

You are elephant hunting with a BB gun, you need to get out of the jungle and learn real estate.Your questions are so vague they can't be answered without writing several books.Land is always valued with the market approach unless it yields income without improvements, then the income approach may also be considered. :)

Many prospective Buyers are looking at sale comps and not income approach on these types of properties when making purchases.

I'll take the opposite approach.... 

However, given that they've also given us a formal appraisal of their value, it's actually also another piece of leverage to re-approach the owner. 

In New Orleans I was on the board of one of our neighborhood organizations, and when approached by Whole Foods they let us know there were requirements for parking, average income, and traffic. 

I went into the house yesterday and there will be lots of deferred maintenance as the owners have taken a very hands off approach to landlording.

There are several ways to get into the property management space without risking a large outlay of capital, makes sense to keep your options open as to the approach you choose.

How do you approach this question?

The way I approached it is by having a local vacation rental management company, I complement bookings the rental management company gets with my own advertisements.In the AZ area I went with a company called AwayLiving.