My wife and I are not regular investors.

They reviewed the reports their manager sent them, got on the manager for things that weren't right, were willing to switch managers and contractors and visited on a fairly regular basis.

Is it supply and demand, rising housing prices, housing shortage or all the above or something else?  

As a result, there is a high demand for student housing and low supply as the University does what they can to accommodate the growth.

Third, the seller can still receive regular returns without needed to "fix toilets."

The property is 100 yrs old and requires regular upkeep.

Show a picture of a dog to a dog lover and that gives you a leg up, especially with the outrageously low housing supply at the moment.

On the other hand, the economic factors like interest rates, affordability, and supply could make the sf home only increase in value in the short term. 

Also keep in mind vacation rental can be done long distance but it is more a customer satisfaction / hospitality market where as seasonal rentals (say a few months) are more like  a regular tenant market. 

You can get regular residential financing (backed by freddie/fannie) for up to 4 units.