Hey Jace,
I'm about in your same position but I actually have not moved to Midland yet but will be in about 20 days.
While I'm just starting my investing career as well I don't have much to offer on the Real Estate side but the reason I am moving is due to my career in O&G and (hopefully) can offer some insight on that aspect.
As far as everyone sees and knows Oil is on the rise, this may not last long however as it's mostly speculation on the increased usage of energy from driving and people generally being more active during the summer months. Some of the reason for the recent crash has been china slowing down economically in their growth and our supply has been greater than our demand. We have "tactical" reserves (really just storing it in tanks) that we fill up that are not available to the market and helps to keep the oil price high. These reserves are almost full which explained the bust in the market a few months ago and now people are speculating that the increased activity will help to deplete the reserves while companies have reduced production.
Keep in mind this is a brief overview, there are many things happening and properties of reservoirs were drilling that add into this equation. I don't necessarily buy the bounce back of oil right now and would give it some time. While that means bad for my job, I've heard many speculate they wouldn't be surprised to see oil tank in the 30's or 20's before we see a bounce back and this would spell incredibly bad news for those selling or renting properties as drilling contracts will be getting cut and people will be moving away but may be a wise buying investment if you hold off until then.
With everything there is only speculation, many have guessed oil will do the complete opposite and everything will pick up again. One thing to note about the reservoir's composition in the Permian is that oil production falls off VERY quickly and the break even price is relatively low for an unconventional play so if a company owns land they are better off drilling than trying to sell the land.
Again, this is the way I see it and my soon to be colleagues see it when we have this discussion and is by no means what will happen. Just trying to pass along some information.
Ian