You make the rules, you inforce the rules, if you can not do that with zero compassion you are in the wrong business.Tenants in lower class neighbourhoods hone their skills to take advantage of every possible system and landlords are just another system in their sights.If you get good tenants obviously treat them cordially but never ever let down your guard, that is what they are waiting for you to do.

Here are the particulars:Purchase Price: 200KMortgage Owed: 182KProbable Sale Price: 230KMonthly Mortgage Payment: 1,600Combined Rental Income/Mo: 2,400Considerations: The house will need a new roof within the next two years I am living in a different state as the propertyThe rental market is solid, with Yale, Yale hospitals and a Coast Guard base nearbyI lived in the house from Dec. 2014 - Sept. 2017, allowing us to take a tax-free profitI do not have enough equity in the house for a HELOC, and probably won't for another yearAm I being shortsighted here?

I agree with @Jay Hinrichs that there are so many "gurus" out there that do not provide value, that everyones guard should be up.  

Not even close.In the weaker suburban to rural markets I notice lenders tend to be the (old guard).

Tenant screening is the best way to guard against this kind of "professional sob story" tenant.  

It took me completely off guard.

I would like to hear some of the biggest/most common problems other investers have had with new tenants, what they did to correct/guard against these problems, or any other advice that might be useful in making out my first lease.

I’ve never had anyone send me an offer before so it caught me off guard, but it’s not even on the market nor do I have an agent yet. 

Ok, so I've only sent out roughly 15 post cards and got a call today from one of my post cards, it really caught me off guard.

You need to guard against seasonal residence taking advantage of the MTM.