Hi @Jeff Alwine Good luck getting started in your investing career. I have a large personal and joint portfolio in Martinsburg WV and Hagestown MD. Those are a mix of self managed and internally managed with an in house PM. To your question, My first property that I purchased was in Frostburg MD. I recently sold one and still have one there and that is over an hour away. I still self manage it and go there from time to time to check on it and get it re-rented. The #1 thing is getting the best tenant for you properties that are further away. The #2 thing is to have a property that has been rehabbed or has been very well maintained. These are basic fundamentals to real estate investing but so much more important when you are further away from the property. Poor tenants and getting nickeled and dimed by maintenance issues will drive you mad! I take extra special care when selecting tenants for these rentals. I have a very solid process for selecting tenants. When I purchased these properties I did all the work needed to make it tenant proof. You should not leave any deferred maintenance that will cause you and your tenant problems.
These are sexy answers but even with property management this will make your life easy. The #3 thing would be find the best PM you can find if you go that route (talk to all of them and get referrals) before you decide. I have decided to self manage for the last 10 years and I'm happy with that decision.