My roof was damaged by Matthew last year and I had a very pleasant experience with American Integrity but I agree, there is a definite need for reform in many areas of insurance. 

- Personally I would not buy a multi family around Boston at this point in time unless you would be converting into condos or found an off market DEAL.

The government is also intimately involved in the real estate market.  

If you allowed them to move in, sign lease and gave keys but did not collect the money at move in time, typically you will have to send a Notice to Quit and proceed through the eviction process to remove them.In which case, is definitely the fault of the landlord for not collecting payment upfront when the lease and keys were exchanged.

It will be tough to ignore like other potentially questionable industries like gentleman's clubs or "intimate shops" because of the sheer dollars involved.  

The classes are very affordable, costing you more in time than money.For someone in your position with no wife, no children, and no overall responsibilities, I'd recommend those classes to hone your ability to handle minor breakdowns. 

I took photos with my phone and they are not photoshopped, actually the prospective tenants will probably be pleasantly surprised when they see the place that looks better than the pictures since  I am not a good photographer ; ). 

Especially since if there is something that the landlord could do to make their stay more pleasant, they should do that.

I will be very pleasantly surprised if I show up on the 15th and they are out and there isn't cement in the pipes.

In short, should you make a purchase based on gaining another rental property, or should you buy what you personally want in a home and then be pleasantly surprised if it ends up being a good rental later on and if it isn't just sell it?