I personally would lean more towards the duplex.

@Josh Madigan Hey josh I was leaning towards the FONCE exemption.

For future leases, just put a clause that the any vehicle must be registered and insured, short and sweet.If you want a lean to added to the side of your shed (assuming it is wood), he could help cover the costs for that with the understanding that it is yours and he can't take it down when he leaves, but he can park his bike under it while he lives there. 

I'm still trying to figure out what will be our best way to start out...right now, I'm leaning towards wholesaling or maybe partnering up with somebody on a flip! 

I feel like any investors using HML in my area are being put on the back burner even if the price is right based off shear convenience..

Right now I leaning towards demoing all of the unpermitted work and starting to rehab the property from that point forward but I'm not sure if that's the right way to go about it.

I don't know any details about your location or the property, but I can tell you that purchasing turnkey means you are paying a premium to get a property rented and ready to cash flow, which means the return will be lower for you because you are voluntarily giving up some of that return for the convenience of not having to do the leg work up front.

Have the end game in mind and invest where it makes sense for you and your personal situation not where it is convenient close and comfortable.

Leaning on experts will shorten the learning curve and help your first investment be a success.

@Mike McCarthy I was leaning towards painting it also.