I am based in Pensacola, FL and looking to purchase a duplex for the purpose of house hacking to get my feet wet in the REI game.

Call it a long-hold fix & flip for land, with an injection of wildlife and habitat minded eco-investment.

If someone sues you and wins, they can only take the LLC that owns the property that was involved in the lawsuit.Best: Using a combination of LLC and land trust to protect your rental properties.

Prime recreational land costs $$$ but burned, scarred and neglected land that is hard to access can be found for a reasonable price.

If you move away from that road and come closer to base or near the hospital, those would be great areas to rent in.

Once you figure out the answers to these two questions, you can start to narrow down what markets make sense for you based on the FRED economic data: https://fred.stlouisfed.org/

Based on peoples experiences in MTR in Denver area, is it a good idea to turn a house into MTR, especially of such size?

Planning should be able to get you started and you may not need to hire anyone at all, or a local land use attorney if it is truly necessary.

I am working on getting financing for land but that has been my weak spot. 

I personally quit drinking many years ago for faith based reasons not necessarily physical.