I will be sure to talk it out with everyone involved to be sure I don't make any rash decisions.  

That seems a little odd, I still send out text messages and I dont have a website.

Two flats are essentially just houses.... they trade like houses and there is a lot of emotion involved.

In theory, yes you could get under contracting adding "and or assigns" but really good odd's that's going to kill a significant # of potential deals.

Odd's would be far mor ein your favor if you just bought lotto tickets. 

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

When you own a couple of units, the odds of there being unexpected vacancies that overlap each other are usually low, but when you acquire more and more real estate, the odds of tenants moving out around similar times increases. 

Per this NY Times article, the average American knows around 600 people.https://www.nytimes.com/2013/02/19/science/the-average-american-knows-how-many-people.html#:~:text=The%20average%20American%20knows%20about,do%20you%20know%20named%20Kevin%3FPer the US Census Bureau, the average American moves 11.7 time in their life, which based upon an approximate lifespan of 84 years, works out to be about every 7 years.https://www.census.gov/topics/population/migration/guidance/calculating-migration-expectancy.html#:~:text=Using%202007%20ACS%20data%2C%20it,one%20move%20per%20single%20yearSo, if the average American knows 600 people and they each move about every 7 years, that means that the average American knows around 85 people that move in any given year.How many of those moves do you want to be involved in?

My take is that a Host should be personally involved as much as possible.