Side note - he'd be better off if his tenants were scared off since they are paying far below market rent!

If I were you I would check the Days on market, and check the Trend for pricing Month over Month for sales and listings in the area. 

Hello Misael, I would do a thorough market research to verify that you can get the rent increase you want, you might find out that the market is oversaturated with rentals.If you are trying to raise the rent $100/mo, 1 month of vacancy ruins your rent increase for the whole year.I would list the property for lease 45 days before your tenant's lease expires, if you have your property priced right you should get some applicants before your lady moves out.

I have never used Mynd but Pete Nubig that runs the Houston Market is top notch.  

IMHO it's a mistake to plan on a very specific market and tenant profile.

Purchase price: $300,000 Cash invested: $65,000 Sale price: $455,000 This house needed a full renovation to compete in the challenging Austin, TX housing market.

I've lived here my whole life and know the area and market very well.

I am an agent so it was simple to negotiate after being on the market for a while.

I have sold one in 40 days and others are on the market. 

Does anyone have a software or method of getting deals that have been on market 180+ days?