However, they're much more difficult to come by and the city is overly tenant-friendly.In contrast, cross the border into Delaware County where I just sold a triplex in Upper Darby for $205K.

First, you don't have any evidence of what the door looked like before they moved in, so this makes it difficult to prove in front of a judge if you ever went to court.

Guests steal things and they have a way of leaving filthy dishes, a filthy stove and sometimes it is difficult to put all the dishes, utensils and pans in the location you want them.Unlike conventional rentals, you income is not guaranteed, you have to pay management companies a super large portion of your booty because not only does a management company have to take care of your guests 24/7, they also have to deal with the cleaning services and destruction tenants leave behind them.You have to constantly juggle your calendar for tenants who want to move their move-in date forward, backwards and cancel.

Cat urine is extremely difficult to get out of carpeting and pads and while there are some good products out there to remove the stains and odors it is still a toss up as to whether the smell goes away forever. 

@Tony Hershiser this is definitely a difficult situation and I know that it can really be a mental strain.

Very difficult to make any cash flow for at least 5 years.

Finding a lender willing to do a cash out refi on an investment property can be difficult. 

@Bruce Runn how difficult are these infill lots to find for new construction in the Twin Cities?

Get a difficult tenant and you will wish you hired a manager. 

My payment won't kick in until July so I still have that 1-month buffer to get this done.My risks here are in 2 main areas: rental income and market appreciation.Obviously, with house hacking, it is generally a bit more difficult to accurately estimate the monthly rent per room.