Give a noob some advice here

Hey all! So to preface I am not in the best place financially. Currently setting myself up to escape a bad relationship. I started looking into "RV life" however mine would look a bit different so I just need someone to tell me if I should look in a different direction. I would be looking into a living quarters horse trailer first and foremost, for a few reasons. One obviously being I have a horse, and I show said horse so it would be nice to have the trailer part of my list for future buys. However I would end up parking it in a long term spot somewhere. Due to the fact I have an awesome career here and I am not quite ready to become a traveler. That being said "here" is the Midwest. How are the winters? Is it doable? Please give me all the must knows now.