I live in Los Angeles where properties are out of my reach so I started to look at Cleveland and then it went to Memphis then to Columbus then to Palm Springs and Euclid on top of establishing relationships with agents in each city. 

Do I want to build a working relationship and transition into bigger deals down the road and use these smaller ones to test out the waters?

Build relationships with active local investors (do your due diligence on them...lots of wannabe's out there).

The only time i'd pay attention to the future increases is if something is changing around that property such as gentrification, new fortune 500 employers coming into town or an area with huge historical growth.

You have to find another source-either a distressed property, something you can improve and up the value to another level, or perhaps develop relationships with brokers and wholesalers who will bring a deal to you because they know you as someone who has the ability to close.

From the brokers perspective some may be leery about the relationship and may suggest that you sever ties all together.

Having a sound agent and a good working relationship is essential in this business.  

Despite the background I have in the area, it is absolutely crucial to visit the area frequently, make good contacts and build trusting relationships in order to get a good 'team' in place.  

Also make sure you stay focused and become very knowledgeable about the market you want to invest so I would try to narrow down the markets that you will initially be investing in, it will be easier to build a team and spot a deal as well as build relationships if you focus on one or two markets when starting.

Is that really worth arguing damaging your relationship with your tenant over?