One word of caution is to be cautious of purchasing condos as rentals. 

I've been advising my clients to be cautious and to have a backup strategy when they are buying homes with the goal of turning them into short term rentals.  

Maybe I am just being overly cautious.

Contracts make them responsible and in many cases you have to be very cautious as you may not even have the authority to fix it.I had another issue where borrower used it as rental and renter didn’t pay heating bill so they locked renter out from basement to turn it onI got a call from housing authority about not providing heat - my attorney sent them land contract and we had no authority to enter the house based on land contract and we had no agreement with renter so they county went after the borrower.Still cost me $200 in legal for that though.

I can’t figure out if I’m being to cautious here.

Use leverage but use it cautiously.

I plan on having a management company, being extra cautious with tenant screening, and paying attention to the better neighborhoods by doing my research and working with locals (I do have a friend from Fitchburg).  

The trick here is that you are going to not only want to find someone with a bit of experience, but also a willingness to work with you (shouldn't be too hard but the first time around you always want to be a bit more cautious).

Having had PayPal shut down a business account for no viable reason (for over 6 months), I would be cautious.

I recognize that mistakes are inevitable and risk is inherent in any investment, so as a beginner I'm trying to be extra cautious and take steps to minimize the impact of potential problems (while making sure to avoid "analysis paralysis").The other factor that I didn't mention is that my wife and I just had our first child in December, so we're still adjusting to everything that comes with along with having a new baby in our life, especially the impacts on sleep and free time.