Another thought/ long term plan I had was to make it a mini unique airbnb multifamily as in, have a silo home, then maybe put an airstream on it and lastly maybe an A-frame cabin.  

Has a fee agreement for him. plus 15 hr term.

That tool really sounds ideal...I think in most major markets now that are either saturated or balanced in terms of supply/demand now more than ever amenity rich properties are a must. 

BRRR, short term rental, mid term, long term, house hack, etc???

Second, in terms of asset protection, LLCs are not invincible, but I think what many don’t understand is that they are not designed to completely shield your assets from liabilities, on the contrary they are designed to contain and isolate liabilities.

As a model, Techvestor syndicates (uses investor funds) to acquire, fit-out and operate short-term rental properties for profit in select markets across the US. 

Hi,I have been doing private lending for a very long time, most of time first lien, some time 2nd lien also.recently came across a situation where first lien is already there on property and there is clause than 2nd lien can not be done on property.Investor(borrower) giving me option that we can prepare a new document for "Equity pledge" this mean conditional equity in property if there is default.I never heard this thing before.any one any input on this.Thanks in advance.

Madison has pretty strict short term rental rules if you don't live at the property, so mid term furnished rentals is a strategy I have seen done here. 

I'm assuming it's a big building so that would be something you should review in the by-laws in terms of what you're entitled to.I would get in touch with your personal accountant/CPA or perhaps a local real estate specialist in NYC (there's a few in the forums) regarding your scenario.

This positive cash flow will provide a financial buffer and support your long-term investment goals.Multi-family (MFH) and single-family homes (SFH) are distinct asset classes with different characteristics.