I don't ask for upfront payment, per se.  

Therefore only $50k is subject to tax as ordinary income, and even less SE Taxes.

I hadn't thought about zoning, good point.I'm not worried about which option will make more money per se, I'm just wondering about the technicalities of converting, and any relation to investment financing.  

Perhaps we can help each other meet our goals at some point in SE Michigan - welcome to the community. 

Even I limit my our fund's lending to certain jurisdictions (mostly states in the Midwest and SE) that we really know well.

Thanks,The property is in the SE, I was able to put a crew together for a roof project that has been completed and I brought everything down to studs and re-wired the house up to code myself.

I know Jersey City is quite openly permissive about Airbnb, but I'm not so familiar with short-term management companies per se.

As to your other question; there are no tax benefits per se if you have the leases in the name of the LLC. 

FWIW - not recommending this per se, but mMost of LI is chock full of illegal rentals (basements and the like).

I am not seeing how it would create a worthwhile tax write off per se (Under sect 179 a vehicle previously owned/used for personal use does't qualify).