Ive known Dave for years now, and the one word Id use to describe him is Integrity.

It is fairly well known... 

You're inheriting those (some known and some unknown). 

True, I am 100% with you on that.The point here is, when you analyze, you do based on what you know now (what is known as a fact today) and on what is highly likely to happened (again from today) and to accept the fact that things might change tommrow.Life happened every day, that’s why  we need to stay firm with our direction but flexible with our approach.having lived through the HORRORS of those years fully engrossed in the industry almost nationwide... it was regional on who did well and who had troubles.. no question well positioned landlords in Portland for instance no issue.. 

You are going to get conflicting responses on this because a lot of it comes down to your plans and your tolerance for risk, which are things known only to you.

Cash flow can be great if you manage it well and keep occupancy rates high, but factor in the added costs of management, cleaning, and potential vacancy dips.

Now if it's a lot of rain, yes, the root systems are compromised but that would be.... well at that point one would have to say God's sending a clear message, right. 

@Ryan Kelly mentions what is known as extended dwelling coverage.  

Drilling a well or building out a septic?

There is already at least one request with a lot of votes for this feature, and you can allocate your "votes" to it as well...maybe Buildium will start work on it after it gets a few hundred more votes.