Looking to sell everything to 1 person instead of 130+ items to 130+ people.

You have code enforcement issue in one of those cities and they do not know you, your life is not going to be easy meanwhile the person who has been there for 10 years and knows the inspectors families name will have a very different outcome than yours. 

What  are the implications to me legally if I rent out to a person that has filed bankruptcy? 

Start with Strategy by @Dave Meyer is a good one to start with or Set for Life by @Scott Trench, but you want new people to pair listening to podcasts and reading books with real-life meetups.

Is this also for the life of the loan or is it only for the first year?

I wouldn't fix a faucet there without a gun on my person.

Furthermore, I have actively been researching and there is an ongoing housing shortage in the New Haven area, a consistent population growth, great property price to rent ratio, some new construction projects in the nearby area of the property and that it takes a certain type of person with great patience and “people” skills to succeed in these type of neighborhoods.

Often the money is the investor relations person who communicates with investors  On the Spark team I’m the deal finder and communicator.

I'm reaching out today because I find myself at a crossroads in life and could use some guidance and support from this amazing community.A little background on my journey: I've been through some ups and downs, starting as a mailman and later transitioning into a CDL driver.

I personally invest here for both the cash flow and appreciation.