I am sure that this has worked out for someone out there, but these are just a few points off the top of my head that stand out. 

Hey guys, so I estimated I would be financially able to try to get an FHA loan for a 4Plex in my area in about 6 months ( again this is all a conspiracy, because I am so new to all of this, so I don't want to sound over optimistic or under, I'm somewhat lost even after reading so much ).

As you know, we'll probably both make more money buying multi units in Central Maine vs. vacation rentals any day, so even buying a few VRBO's here and there for fun and to  have a place to crash doesn't really make alot of financial sense.

Standing at the bottom you can not see that last step.

Time will tell, but seeing as this isn't Zillow's primary business, it doesn't have to stand alone and can complement the company's other businesses. 

Talk to your accountant and see what they recommend based on your financial situation then talk to an attorney that forms entites and see what they recommend based on what you will be doing.

Hi Saumon - congrats on getting on track to financial freedom!

@Joshua Meade I got a lot out of watching Spencer Burton build CRE financial models on youtube, specifically his "Watch Me Build a Multifamily Real Estate Model" video and a couple others.

My end goal is to have passive income and financial independence when I finish my career (I love my job, don't want to leave early).But as I was saying; I already have a BS and now have a chance to get my masters.

I would suggest solving your personal financial problems first, then possibly team up with a seasoned investor for a bit to gain experience.