I myself am looking to make my first REI purchase, so take this with a grain of salt.

@Andrew Postell you gave me some food for thought

You say he was living with you, were you paying for his food and other expenses as well, or was he supposed to have another job to pay his bills while working for you for free?

His deal was he worked this small town for 25 years and had customers that put lots of food on the table.

If I find a home in a city that I am not familiar with, is there a quick way to estimate rental prices in that area (other than Zillow as you mentioned, grain of salt with that one haha).

Also your experience as a PM could be your food in the door.

Might as well get a second job in retail or food service. 

When it goes higher, now you are collecting from housing authority AND from the tenant. 100 or 150 might not seem like a big deal to you and me, but if they are paying utilities and food AND it was really cold for a couple of months you might not collect anything from them.Find out what the tenant is qualified for in terms of rent assistance AND what the building is qualified for.

I do wish I could hear more stories from SINGLE female house hackers to put my mind at ease or give me tips.3) Pets: My 12 year old dog/daughter loves people and other animals and traveled everywhere with me, but I do have concerns leaving her in the home with someone I feel is not familiar with dogs (may let her out, give her unsafe foods, etc) or someone that may harm her.

Barcelona and Spain is still one of the choicest holiday destinations and it has good weather, food and a beautiful culture.