We want to begin by house hacking with a duplex in order to eliminate our current rent payment and have more cash to invest. 

@Jake Little what state is the property located?

A SFR was built in 1947 and required renovation.The 2nd parcel, which is right next to it, is an vacant land, no address associated to it.My initial thoughts are:1.Purchase this property and rent the house after minimum required updates 2.

Without knowing more details about the specifics of the project being proposed as it relates to your property, it's hard to say if there are any obvious big red flags that could negatively impact your property's future value.That being said, I would try to find out as much information as possible about the new apartment building's design and layout - the two big things I would try to ascertain would be the location of the garage entrances/exits, as well as the location of any outdoor amenity spaces (pools, terraces, dog runs, etc).  

The rents in that area are pretty good.

Should i form a LLC and collect rents under the LLC?

It raised a couple of questions in my mind about the risks of wholesaling, namely the implications in the event that you assign a contract and the buyer backs out.It seems to me that Paid at Assignment would both:Result in committed assignees, otherwise they would risk losing the money they paid the assignor, andProvide the assignor with a significant cash cushion against breach of contract if they cannot locate another buyer prior to closing, and ultimately decide to cancel the contract with the property owner.But this raises another question. 

He gets an option to buy it for the remaining balance on the mortgage, and pays my mortgage down.Call it rent to own, or call it a loan with free rent as interest plus option to buy.Will it trigger due on sale?

If it is considered a security in Florida, I'm told that a Transfer on Death document can be recorded in the land records of the jurisdiction where the DST property is located to ensure that the interest will not pass through probate even if it is not held in a living trust.

Sold for 155k, my investor plans on doing some light cosmetic updates to bring this back to life and get it on the market for rent asap.