I'll admit I don't really understand why an agent would want to help me find such cheap properties so I'm not exactly sure how to begin finding an investment agent like this.

Most are flimsy, thrown-together with uber cheap materials. 

If you're gonna spend your money in Cleveland on some cheap properties, you'll want to learn the ins and outs of all of the neighborhoods.

I was looking for something cheap, but nice at the same time. my real estate agent pulled through and found this property being sold off market.

If they did what they were supposed to do, the properties you could rent to them wouldn't be anywhere near as cheap as they are.

I love house-hacking for Tampa Bay for a few main reasons: 1) great long-term outlook on appreciation; fundamentally strong market and growth projections, 2) diverse opportunities of house-hacks from luxury house hacks, cheap house hacks, room by room, STR, MTR, etc. 

If I may, let me offer some tactical advice and then some unsolicited general advice.Tactical advice: marketing to traveling oil industry workers probably isn't radically different than what you have been doing to get your rooms filled with students.

What some of my clients have done in the past is look for more creative rental avenues to be able to charge a premium on rent such as the traveling nursing niche like furnished finder. 

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

I travel quite a bit, but I am primarily in San Diego.