Congrats on finding a roommate and learning a little bit about the biz all at once.Hope it works out and you avoid the whole getting murdered thing that would really be a hurdle in your investment career.

I ran into this hurdle once and it took some additional research on my part to figure it out.

Using a 203K is a great idea as long as you don't mind the hurdles to getting the loan.  

The lack of available land or sites that haven't been overpriced for development is a challenging hurdle for a new developer such as myself.

I would like to buy my first property with a low money down option (yes, I'm reading @Brandon Turner's book), and need to overcome the initial hurdle of fear and uncertainty as I dive into this new world of REI.

Fannie Mae realtor us being unreasonable.

Merely "treating" a piece of land as yours will not satisfy the hurdle to take land under AP.  

I'm new to investing and I've been thinking about doing some contract assigning to start out and build some capital, but I have this major hurdle that I need answered.

the big issues there........ the government is corrupt as hell. especially in the muskegon heights area. my brother has had no end of trouble with these people. also, other areas of muskegon, such as the city, they hire out their inspections process to a place called safebuilt. these people are worse than the government over there. my brother sells a lot of his houses on land contract. these people simply refuse to accept this as a sale and call his houses rentals. they claim this gives them the right to issue him tickets for repairs needed because he is the " current owner of record". they use a portion of the government system that is outdated and has inaccurate records to claim he is the owner. consequently, he winds up in court all the time with new " violations" on these " rental houses" that he has full proof that he sold years ago. as of yet, he has be able to beat them in court just by proving that he no longer owns them, but he is going to court almost every week with them. i believe they hope he will just give up and pay the fines. that is not gonna happen with him......lol. but, just so you are informed, muskegon may appear to be a good place to invest, but you will have serious hurdles to jump over on a regular basis. 

You are contemplating a reverse so you will actually get to double dip the NOI on all properties during the 180 days.I would say the biggest hurdles are going to be what your perceiving - the need to sell in 180 days.