Questions from a true beginner on out of state rental searches

[Christian Conti]

I don't know that I can even classify myself as a novice in real estate, as I have just started the process of doing some research after listening to a couple episodes of the BP podcast. I am currently based in Vermont but due to a number of factors in the state (property taxes chief among them) I really do not want to purchase anything in the state and intend on moving out of state in the not too distant future (ideally to a state with much friendlier property taxes). In the meantime, I have been considering purchasing a property (most likely single family or small multifamily) somewhere out of state and use it as a rental property until I am able to move out of Vermont, at which point I would move into the property as a primary residence, or depending on what type of income I can generate from it during that time, keep it as a rental and purchase something else. 

My first question would be if this sounds like a wise plan or should I have a primary residence in the area I am buying a rental property first or should I just jump in a get a toehold with my first rental property and just build from there?

My second question is what is the best way to go about finding property in an area where I am not living? I have obviously been looking through a lot of online listings, but sifting through all the pertinent information on my own over the internet seems a bit overwhelming at times and I feel like I don't have a real starting point. 

Any input or suggestions would be greatly appreciated!