@Aman Kumar and @Nelson Ellingham I am always up to connect with new people, kind of why I am here lol  It's good to keep that momentum of interest going.Do either of you two own anything at the moment?

When managing a rental property, here are some common maintenance expenses to be aware of.

House hacking is not only a phenomenal move for investors starting out, but it's a common strategy in expensive markets like Boston.

I dont believe there is any kind of HOA or ruling organization for these group of houses but it has me concerned that if one day they all decide they want to repave the driveway or add lighting or something along those lines, they would try and make everyone chip in and pay their fair share. 

A person living independently or a group of persons living as a single household unit using housekeeping facilities in common, but not to include more than three persons who are unrelated by blood, marriage, adoption, or foster-child status, or are not Life Partners.Splitting the building into two 4 bedroom units is not allowed. 

Here's some generic guidance.Software is a common question on BiggerPockets.

You'll get all kinds of advice from novices here- good and bad.

Utilize a 1031 Exchange: Under IRS Code Section 1031, you can defer capital gains taxes by reinvesting the proceeds from the sale into a similar “like-kind” property.

Agents pay for insurance for these kind of things.

Thanks for the kind words!