Here in WA I bought basically the cheapest 3/2 there was, I’m beginning to wonder if the price of houses here makes it that much more difficult to get into another one.

If I were to go this route I would clearly identify each of these risks individually, understand how the Govt would potentially challenge each of them and then assess in your particular fact pattern how you would effectively rebut a challenge to each. 

(Only if you are SERIOUS about real estate as your wealth/career vehicle.)Make sure you join a brokerage that is large, established, and has a reputation for top performance and excellent training.Once you learn the basics and get out into the field to see the state of the market, you'll learn the price points and be able to know a good/great deal when you stumble across it.I have made some of my best (most lucrative) buys from meeting with a seller who wants to list, and when we discussed the price, I knew it fit my parameters, so I bought it! 

Basically, they guarantee your principal.  

In addition, he also informed me he is not on contract to render me 1099 filing support and basically said I'm not going to help you, good luck on your own.

@Christopher MorrisTo assess a market, consider population growth, job market, economic growth, rent-to-price ratio, cost of living, school districts, and growth benchmarks.

@Jon Fletcher There are basically two potential options. 1) Amend the tax return in the year of purchase and prove you used capital gains to purchase the property and 2) Sell the property to an OZF, follow the 20% related party rule and then the structure of the sale of the property to be able to reinvest the gains.

It will familiarize you with the basic terminology and benefits.

Are there any books or resources you can recommend to get me started with the basics?

Assuming the insurance premiums don’t significantly impact my cash flow (which is one of my primary goals), how do you assess the risk of taking out a loan under my personal name versus opting for a commercial loan that requires a larger down payment and comes with a higher interest rate?