For 1% investments you'll be going closer to Worcester, Fitchburg, and other further markets bc the prices of your regional market is climbing.

Depending on the furnishing and amenities, it seems probable I could get closer to that $80k number.After I move out, I can no longer operate the property as a full time STR, so I want to switch the strategy to MTR.

So for high season, I am always priced higher than my competition and wait closer to season to adjust if I'm not getting bookings.

You could also do a walk tour through the facilities any ways to get a feel for the competition.The good thing, if as everyone has noted to you, check zoning; you are closer to the population than all of them. 

Quote from @John Mason: See if you can find time to fly to meetups in hot markets too I am trying to find my first one something closer where I live so it's easy maintain, but I ll keep in my mind. thank you.

But there is hope... if you drive through the 4th ward area, you can clearly tell which properties are owned (single family homes with kept lawns and neatly decorated) and which properties are rentals (usually a broken window or two, falling apart porches, messy yards)... the closer to the single family-dense parts in the 4th ward, the better chance you have of getting a rental property that hasn't been laid to waste that you can purchase for a fairly cheap price. 

@Olu Oguntoyinbo Its more difficult to cashflow the closer you get to NYC.

pick a market this way.a place you used to live in, or went to college in, or have family, or like to vacation in, or know really well.also: consider investing closer to where you live. 

Markets closer to your back yard are easier to get started in.

I had to grade and level the entire property and plant new grass and it's now one of the prettiest lawns on the entire black.