First Deal - Afraid to make a move!

[Theresa Reynolds]

Hi everyone! I am a newbie in Montana and wanted to see if anyone on here is familiar with the real estate market Montana, who is willing to share their experience and teach me some cool stuff :) 

Currently shopping around for rentals in Helena/Great Falls/ small town Montana, preferably Helena but would also be open to partner up with someone more experienced on a flip or two to increase my budget.

I am particularly struggling with just making a move! I spend all my waking hours on zillow and see potential listings but can't get myself to move forward. I've been doing my homework and studying up on rental investments, but I am afraid of taking risks and don't want to mess up. I am also currently looking to buy a house for myself as I am living in a crappy rental, and want to be able to to that as well. I am a first year teacher, so don't have a lot of income but I have about 40-50k from selling my old house to play with, without jeopardizing my personal savings. Can I buy two properties with that? Ideally I would like to find propertied with a cashflow of 200-300$/month. Am I aiming too high? 

I would love to hear your "first deal" stories and would appreciate any input or mentoring!