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)?

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.

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

James, I tried doing this in another city which I was not a member of their mls, after signing the contract and paying the fee, there were a lot of additional charges, like they wanted me to pay for the lockbox and shipping fee, I had to take the lockbox to the property, in the contract they said they will post 15 pictures, but they wanted me to provide pictures they would just upload it.I'm just trying to say double check and make sure what is included and what is not, if you are in town, it will be a lot easier but for my case, I didn't want to drive few hours to run their errands.

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

We have seen the days on market slowly come down, but it is still high compared to previous years.

I might wait until the picture becomes clearer regarding the city's newly liberalized building code which will apparently allow the use of CPVC and/or PEX water supply piping.

Being able to do min one week stays would be nice if that would allow the property to generate more revenue.If the property has already appreciated a fair amount in 2 years it would be a bummer to sell now just because the rate is high.