So lets say you rent for $2000 and have $1900 in expenses.

You can run the same scenario accounting for the tax hit if you kept it past the 2 of 5 year time frame I presume you are referencing. 

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

You should get more nights in the smaller property that can still easily accommodate a family traveling, but is still inexpensive enough to make sense to solo travelers.Cleaning fee impact: Don't you collect this back from your guests?

We were lined up to have this project complete by August which would still be in the prime time frame for selling this house.TLDR of my previous post - I ran into troubles with my first flip which was going on at the same time as this project.I had to pull my contractor from this house to save the day on my first flip.

You can program individual access codes to work only during a certain time frame.

As for the third target market, Sacramento is close to you, it's a state capitol, relatively inexpensive, two major universities, great local culture...

A place that is easy (and hopefully) inexpensive for you to travel to a couple times per year to check in on things.  

Hello Mike, It is nearly impossible to answer this question without taking a deep dive on the numbers of each but often times in expensive markets like Seattle the cost of construction is so high that it doesn't make sense to tear it down unless you can build something way bigger/nicer.

PM's are always looking for good inexpensive cleaners.