Are you happy with the return on that investment and do you think it will continue to appreciate (highly dependent on where you are at in the Bay Area)?

It was built in the 60s but just got a new roof, HVAC and water heaters were all updated between 2017-2018 so fairly new, and it’s an active mid-term rental making about $3,200-3,600/month depending on the season and he provided all the documents to support that from the past 1.5 years.

On the other hand  If you know the markets that are more favorable and attract high qualities tenants land lording can be very easy with little to no worries.  

Where my primary residence is, cash flow negative, entry point for anywhere around here is too high, and I like the market out that way.

One thing I'd keep in mind with mid-term rentals is I expect the mid-term rental market to get highly saturated at some point just like the STR market has.

Since it's the ceiling, when your plaster man is finished with the repair you can bank on it it's going to need special primer to hide the water stain and a respray of the ceiling color.

So, either the purchase price is very high, or your expenses are high. 

This will pressure up the rents.We saw a similar tight supply in sales as well.

Especially if you have a short high season which is also the time that you want to be there.

To @Bruce Lynn point, the rents are not high compared to house values right now - shortage of supply is driving up the prices.