It has a larger population with a stronger job market and a college that would drive rental prices. 

Sounds like your first task is read local law.

If you want to save money on this step, you'll want to take over this task yourself. 

I am looking to buy my first rental property but its a daunting task.

You have long term and short term holds but by building a larger portfolio you increase your total monthly rental income. 

If you haven't yet bought a property, I would focus solely on that task first.  

When this happens to me, I end up selling the property and moving to something larger. 

I think it would be helpful to have some kind of assessment tool to evaluate larger cities' markets based on inventory, average time of properties on the market, appreciation rates, etc on a yearly or quarterly basis.

I wanted to cash in on the equity and trade up to a larger property.Purchase price: $1,250,000Cash invested: $50,000What made you interested in investing in this type of deal?

I think you're making the right move here to address this in a proactive manner as opposed to reactive when the problem is larger.