@Joshua TanWe have access to a Landlord insurance program that includes 2500 deductible, 1 million liability, replacement cost, loss of rents, and water back up that is very competitive in price.

It all comes down to your personal goals, risk tolerance, and access to capital. 

I had some thoughts that can't get off my head, but I know there are a lot of experienced and knowledgeable personals on this platform so I would like to ask everyone their thoughts on the route an aspiring real estate developer should take.

We also retain access to 80% of our equity, so it really maximizes our flexibility.

The pretty clear-cut answer here is this:  You'll want to be in a structure that provides you the most robust legal protection, but you'll want access to the best lending options. 

The barrier to entry is high due to pricy API access, but this could be extremely lucrative if we get it going!

Take advantage of the networking opportunities and best wishes to you.I really like the alerts feature that can quickly guide you to current topics that may be of interest: http://www.biggerpockets.com/alertsThere are a few self-contained guides that you can access here: https://www.biggerpockets.com/guides

You will meet lots of great vendors, wholesalers, title, Realtors® and have access to tons of meet up groups and education.

With this being the case, that means that the most that the lender will give you access to is 85% ($205,600) of $257K minus your current balance of $138K which yields $6,600 under the best-case scenario. 

Totally agree about the access to CTA lines--one of the greatest benefits of living in the city--having a world class, reliable public transportation system at our disposal.