Turns out the contractor was right so now they’re going to have no choice but to replace it.

My choice would be to mortgage and pull out every penny possible or sell and start over if they do not cash flow with full leverage.

In regards to starting an LLC, would you need to set up a new one for each individual property?

One was I could lock in the rate for 30 years and not worry about a ballon on a commercial, also if I decided to sell any one of the properties I could sell individually.  

It's the safest way to begin imo and a great choice for your first investment.

JohnAn LLC is a pass through entity so it is taxed on the individual level not on an entity level.

As far as the loan, I was considering going with a Military Choice loan from Navy Fed as they do not require any money down and will do 100% financing to include fees.

If I buy a property in a Land Trust,Or if I originate a note in a Land Trust,Then sell partial beneficial interest in the Land Trust to multiple individuals,Do I need a PPM and need to have this passed by the SEC ?

The house is old as well, with some issues (all 3 furnaces will need to be replaced within 3-5 years).What would be the wisest choice for a first investment?

That being said, many of the smaller towns along the coast and inland have a smattering of multi-family properties, which may be a better choice if you're concerned about school district, etc.