Did you find it confusing too and do you feel this is just part of the natural learning curve? 

It is not a measure of your quality of character if you do not naturally know how to be a good landlord the second you hand over the cashier's check to buy your first investment property.

The architectural style of the house makes it challenging to put gutters around the front roofline  due to some overhangs ( 2 on each side of the house that goes straight out in a rectangular shape like an inverted U shape but with sharp straight corners and there’s 1 middle overhang that’s like an inverted V shape that is also attached to the roofline and come straight out of the front so  rain water will come from those as the overhang covers a portion of the front and will kind of serve as an extension of the roofline. 

Next time I need some quality free research, I will just publicly challenge my friend @John Hyre.

And you should have something in your lease agreement about immediate notifications for any water leaks of any nature and the consequences of tenant not doing it.To summarize: it depends on the roof condition, the insurer and your financial planning, it might make sense and have options in replacing the roof, or might be better to do repairs and postpone replacement.

Transitioning from the previous landlord's rental agreement to yours may be a challenge for them, or may not be. 

On cape cod the zoning  for a cafe/food establishment is very challenging.

We just got an offer accepted on a Condo on Kauai and our next move is to purchase a multi family in the Beaverton, OR area.I’m hoping to network and gain valuable insight from this forum as well as provide any personal success and challenge experience from the standpoint of an active duty military member who has purchased and sold multiple homes.

Jesus,Don't take any of this as legal advice, it is just friendly advice, but there is nothing wrong with an assignable contract, depending on the nature of the property you are purchasing.  

Generally, the biggest challenge is a lack of quality comparable properties.