Values for nice homes are driven by what other owner-occupants will pay, not what investors will pay per dollar of cash flow.

Taxable Value has a cap depending on the state of how much the taxable value can increase based on occupancy.

I will be retiring soon and am eager and enthusiastic to learn about this world as my post-retirement occupation.

Some banks have very specific listing requirements where the property has to be on the market for X  number of days before reviewing offers, some have an owner occupant period, etc. 

Your occupancy will (likely) be much lower in the shoulder season and non existent in the low season, except for maybe the holidays.  

The reasons that come to mind to me are poor rental history and/or planning on having occupants not on the lease.I think typically for a college town you will have a much higher vacancy rate - since demand is very low for 3 months. 

Be mindful that Dodd Frank applies if you sell to owner occupants.  

My 8 unit loft building I've been at 100% occupancy since purchasing it only two years ago, I've increased rents from 7K a month to 12K per month.

If an assumption of a vacancy rate is not met ( for instance in a year you have 100% occupancy?

Occupants should own the homes (and maintenance) and park just charge lot rent.Find the prevailing lot rent for this area.