There are slight Regional variations in labor prices, but it's not as large a discrepancy as people think.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.

Would love to connect with people who can give me advice on what to look for or where to study for starting out.

Though I have purchased some with a mix where 330+ days a year, people parked in the driveway and the street except when there were snow bans, but there was enough room to fit everyone in the driveway/parking lot, and that was a hassle to deal with some days. 

Too many people get stuck in analysis by paralysis and then before they know it it's been 5 years and they are in the same spot Do you think my age will impact my authority as a landlord?

I am completely new to the investing side and would love to find something to meet new people/learn as well as learn more about the city. 

I put quotes because its simple but many people make it more difficult.

I've heard horror stories that it's usually impossible due to the "burden placed on the municipality" but could really never understand what that burden was... most people living in those units wouldn't be using the school systems so aside from maybe an increased volume in emergency medical situations I can not understand that statement? 

Because Airbnb only makes money when the guest books on Airbnb.Hence, they want the price to be cheapest on their platform, so people book on Airbnb instead of elsewhere, and want their properties to be able to compete with hotel prices (even after cleaning fee and service fees). 

However, a few things you could do: You could talk with them & learn more of their story to figure out why their credit score is low as well as the type of people they are.