First timer - opinions requested

[Kristen White]

Hi everyone, first post. 

I have been wanting to invest in real estate for 30 years. This week in my rat race commute I started listening to audio books about investing. I oddly enough started with Rich Dad, Poor Dad, and then went on to three more books from Bigger Pockets publishing who all mentioned that book. I was raised by "Poor Dad (parents)" who taught me those concepts growing up, and is still mostly their values, but they were also lucky enough to have lived in a time where that worked well enough for them as they retired with a very nice nest egg. In these days and what my life has been I will not be able to repeat what they did and even survive. 

After that book changed my way of thinking, the next three told me I can (finally) really do this!

Me: Newly remarried, I make over six figures, he makes more than twice what I do. Both in IT. He has stellar credit but is unable to make deals due to the sensitive financial company he works for and the amount of student loans he cosigned for his kids. I have really bad credit, thanks to being a Dave Ramsey follower for a decade but very little debt. Seven years ago before I met my now husband I was a struggling single mother supporting four kids on my own. My parents, being wonderful caring parents, purchased a large house in cash for little money through the family trust for us. It was a fixer upper with wonderful bones. It was written legally that I am able to purchase the house from the trust for the original purchase price. (Meanwhile I had to pay a "rent" that went into an account for major repairs) Me wanting a nice house to raise my children put a LOT of my own money in for cosmetic repairs and the house is now worth more than double the original purchase price. $219k - now $500k market price in very southern Maine/NH border. Five bedroom, three baths, and yes the comps support this. Actually the comps say $600k but I don't think I could get that as it will need a new roof soon and there is asbestos siding that is still in good shape, but it is still a liability) I am still in the home until my youngest graduates in three years, but she is the only one left and when she is not with me (50% of the time) I am at what will be our forever home in NH. 

Most of the homes in my neighborhood are similar to mine and have all been converted to multi family homes. As my first project I would like to purchase the property out of the trust, maybe move into my newly formed LLC, and convert to a 2 family. With going rate right now, as I am friends with other owners on my street and have their opinions, I could easily get $1800-$2k/month. We would stay in one of the units until the youngest went to college, or moves on. We are near a major college campus and a large naval base as well as the best school system in the state so it is a highly sought after area.

How would you go about doing this? Also adding, I have spoken to my parents and they are all in for being creative with our arrangement. They are just looking for return on original investment but taking out of the trust at some point is a must as I have an AH of a brother. (if something happened to them I have a year to get the house out of the trust)