Hiring a lawyer sounds expensive, but it is way cheaper than hiring a amateur (in this case yourself) who costs you money and provides no results (and then you need to hire a professional anyway).My personal philosophy is to "do it right, or do it twice" and its way cheaper to do it right once. 

You do that then you could have a lot of cash available to finance your next purchase and perhaps renovation costs as well.

Purchase price: $187,000 Cash invested: $15,000 Sale price: $259,000 I got tired of moving place to place and worrying about finding roommate, security deposits and not having enough money to deal with maintaining someone elses home.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Pricelabs costs but the ease with which all the comp sets are gathered and updates both calendars on Airbnb & VRBO make the subscription worth it to me.

No deal(s) just insights & offers to obtain a premium membership that cost ten times the membership you already have (with monthly or annual dues).

Are there risks or hidden costs I might not be considering?

You can also try the travelling nurses route, a lot of them are looking for low cost housing when in town. 

In other words, you will incur the cost of demolition just to get the raw land.  

The Highway 64 property presented a great opportunity due to its low acquisition cost and potential for substantial value increase.