@Bridger L Logan me and my wife started off like this.

But in terms of a new home builder wanting to buy 109 acres in that location - I just don't see that being very likely (IMHO). 

What's your credit score looking like?

@Guillaume Vidallet I'll chime in here since it seems like everyone answered your question and gave some great advice.I'll suggest that whether you have one LLC or multiple LLCs you have separate bank accounts for each and make sure not to commingle any money.

I'd like to understand which is the better option between these two and the reasoning behind it. 

Sounds like you have some interesting options, and good reasons for both! 

However, these costs can often be added to your property's basis, which helps reduce capital gains tax when you sell the home.Once the property is officially a short-term rental, subsequent repairs and maintenance would likely qualify as deductible expenses. 

But boy does that seem like a lot of guest stays per month.   

Jersey City is hot right now but like I tell my clients the majority of the time I can find them deals that make more sense in Essex County but that depends on the client and what their needs are along with their comfort level. 

If it's not usefully less than 1100$ a year, there's no reason to switch.sounds like Xero?