In the example you outlined and in the case of what a lot of people are doing right now (super high LTV underlying, negative equity on wrap, 100% financing for the buyer, low note rate, etc), then no, this wont work, primarily because whomever created the wrap note is either an idiot or a fraud.  

In the end, you have to decide the cost / benefit / risk / reward of doing one makes sense in your situation.COST - You have outlined some of the costs, but not all. 

Meet with a local banker & schedule a time to talk with a mortgage broker, they'll give you at least a baseline of what kind of down payment options and rates are out there.After that, if you're still wanting to research more creative options, do some looking into seller financing (a very hot topic with good, and bad, advice out there), look into private lenders, and commercial financing options.If you're wanting to live in 1/4 of your quadplex, then conventional residential loans may in fact be your best option as you can purchase that with a fannie/freddy loan with very low down, and use up to 75% of the income from the property toward your own income. 

CT isn't cheap so if you plan on doing it there you are going to surprised at how poorly you do. maybe in the suburbs I'm not sure but as much as I know people call us from CT and everyone is rich and has lots of money and things are expensive out there. build to rent is a great model. we build 3 story walk up infill and keep it to the residential side. 3 units is the most units before it's commercial and you need engineering, etc. check comparable and things liek that. we came up with this design a year ago and we sold 10 if you want to talk further please DM me happy to connect. there are some great build to rent conferences. we went vertical not horizontal with it to save on build costs and design to fit on any infill lot. this fits on a 3500 square foot lot. most lots in our area are 30x120 or 30x150. in miami where I live now they are 50x100 or so. but any infill lot we can pretty much get this one on. there are some great build to rent conferences coming up too that if you like this topic I'd recommend attending I'm sure you'd learn a lot.  

Most likely your conclusion is correct, but the only way to confirm it is by having a real estate accountant review your tax situation.Also, please read this introduction if you want to better understand the concept:https://www.biggerpockets.com/forums/51/topics/1075919-five-...

I've house hacked twice starting at 22, and here's what I learn and what I regret: https://www.biggerpockets.com/forums/922/topics/1133476-hous...Hope this helps! 

@Dylan Ray just south of you.https://www.biggerpockets.com/forums/521/topics/1225233-ocre...Good Investing...

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.

Quote from @Jay Hinrichs: @James Hamling@James Wise@Steve K.Hey guys interesting new law from State of Oregon on wholesaling and we know this is a huge topic on BP.. 

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.