The reason l'm looking into the Greater Boston are is because l'm from around the area(Belmont, MA specifically) and New London is relatively cheaper to get started compared to Boston from what l have seen. 

You're one step ahead of most of those starting off, and that's by identifying what you're wanting to start with.

Hi Zoe, welcome good for you to start early, time is the most important ingredient with investing.

In your opinion what do you think is the best property to start with?

I have saved up some money but my goal is to save up at least 20k in a year before I start looking for options on house hacking in a duplex.

To start you need money, Your money or someone elses.

When my wife and I started out we new we wanted to invest but did not know how to, we took action and unfortunately found a family friend realtor (amazing learning experience) then we found bigger pockets. 

And to answer your question, yes, DTI issues are usually why investors start using DSCR loans. 

I'm curious what more experienced investors will leave to finish repairing after they list the property, but before they start to show it (or lease it).I start the marketing about two weeks prior to completion, with an advertised availability date of one week after completion.

Quote from @Lee Banks: Hi my name is Lee I'm looking too buy my first rental property and but I feel as if I need a mentor to watch, I still need to learn the basics of real-estate does anyone in New York do programs or mentorships and where would you start if you first started real-estate today  Hello Lee,I'd recommend looking up local meetups here on BP, meetup.com and, eventbrite.You can also call around to speak with RE investors and professionals in your target market to begin making connections.With so much available information online, I'd recommend speaking to a few people and doing independent research before committing to mentorships.