I wanna to approach the owner but I am not sure what is the best strategy for me.

So you really, really need to play the exit game and look at each unit and say " If I approached this tenant for a rent raise and they had to get out how much per unit would I have to put in to land a new tenant?"

Your advice is so narrow minded to full time or homebased investors I can't believe that I am the only one that ever sees this when they read your posts.I will never personally throw away a 15% COC return because it doesn't meet some ridiculous forced appreciation projection, or whatever other mathematically self-stroking overly analytical criticism can be thrown at it.  

@James Wise and I had a nice chat about Turnkey Investing and how his company approaches it.We also talked about different reasons for becoming a real estate agent, something James recommends. 

How does it work if I am trying to sell my own property and a buyer approaches me but has a real estate agent??  

I think for the house hacking approach the first goal should be to have your tenants paying for your expenses so you're able to live there for "free" So if you'll be making enough money from rent to pay your regular bills like the mortgage, taxes, insurance, utilities, etc. and can put the excess money and your own monthly "rent" contribution aside for cap ex and other maintenance you'll be in good shape.

Thats a very interesting approach!  

@Dawn Oree If you approach insurance agents with the above statements, you will get all sorts of different policies and you will be comparing apples to oranges. 

Like @Ann Bellamy mentioned, my lease also specifies that all payments will be applied to outstanding fees before being applied to back or current rents.What I am unclear on, and I would greatly appreciate input from others, is whether or not I can simply send updated lease verbiage to tenants whose leases have expired (and are therefore month-to-month), without getting their signatures, or if I have to take the time to approach each of them individually and get them to actually sign the new lease.

The bank valued them at 350k which is a lot lower than expected but they are using a combination of price/sq ft, replacement cost, and income approach.