I have an ice dam at one of my properties that did some damage due to lack of insulation so I was planning on going down to Home Depot and getting some insulation and the blower this weekend.

For a landlord, ongoing maintenance is just a routine part of your expenses.  

Top dollar goes to the ones that have a nice view, close to the train, and in a relatively safe neighborhood. 

If it is not all city, I would probably walk, as there really arent enough units to shoulder the ongoing maintenance costs. 

Its can be very painful at time working with people and training them. 

How is the east riverside area now that the train fell through.

If tenants are actually OK, or capable of being trained, then you got an extra bonus.

Many agents hate working with investors because they are 1. embarrased to submit low ball offers and 2. it's a lot of time and most investors won't even close on a deal with them - especially if they plan on going unconventional routes like assigning leases etc.You need to find an agent that specializes in working with investors - calling up a top producer at a random office and or even a newbie isn't going to do you any good.Instead I would call the office managers and ask them who specializes in foreclosures/investors and they should give you some good reference points.

But you can also get stuck planning and planning and planning, and never ever doing.I know, I was there...I bought some books, a couple courses, went to a few local boot camps, trainings, yada.

And this is one of my biggest ongoing problems… I feel (my opinion here) that many people in the “trades” are very good at what they do as far as skill goes… But, many are just terrible business people… This is true for many businesses not just contracting.