I incorporate this cost into the lease or agreement.

Some unincorporated counties, that traditionally are more laissez faire about land use than incorporated cities, are starting to restrict or outright prohibit short-term rentals. 

Ok, so what are the pros and cons of incorporating and choosing S-corp vs creating another LLC and electing S-corp taxation? 

You need sewer, water, electric, fiber optics, sidewalks, fire hydrants, storm ponds?

Outside of that I'd say I think even if your plan is to sell to a rehab-buyer you need to run the numbers yourself so that i.) you better know whether anyone will touch this or ii.) so that you can incorporate your numbers into your pitch to buyers.I would try and estimate pending housing appreciation rate.

The project's primary goal is to offer comfortable and affordable living spaces while ensuring the property adheres to Pretty Good House principles and incorporates the sustainable building practices championed by experts like Joe Lstiburek and Allison Bailes.

For this property, you would be wise to incorporate the income from the other units against your debt service to make the property more attractive to lend on.

#2: If I had work done by a contractor who was Incorporated (e.g  ABC Construction, Inc) of over $600 do I need to do a 1099 for him?

Also, S-Corps are apparently more corp-like, and its not advisable to hold real property in corporations.

I told her to incorporate that into the loan repaid amount, and she immediately did and asked for my ID and bank statementsNow most lenders do 80% financing with a 20% down payment, which at that point, I understand why there's an upfront cost.But if this is a 100% financing agreement, why are they asking me for anything upfront?