Hey Rohan, I'm working closely with about 5 investors and I'm at the stage of developing a rock solid relationship with a contractor.

As a buy and hold landlord, with middle and slightly upper middle class tenants in relatively new properties in above average neighborhoods and professional property management and solid property and liability insurance (w/ umbrella ins as necessary) I see absolutely no need for an LLC.However my risk profile is different than yours, so there you go.  

As a lender, I see this as completely bait and switch unless they provided you a solid reason regarding the approval. 

Fun fact: CoreLogic got busted for selling the Austin Board of Realtor's MLS sales data to the Travis County Appraisal District in 2019, so up till then the tax assessor was using MLS sales data.I would assume the tax assessed value to go up to at least the list price of the home and if its more than your purchase price, you can protest your property taxes and use your HUD statement as evidence as @Rick Reeder suggested.There are no $ or % caps on how high they can raise the tax assessed value. 

I'd really like to have some solid knowledge on this before doing a 1031 exchange as depending on what the deal is, I may just keep the current rentals.  

@Shiloh Lundahl - Not too well connected as of yet with other investors, but have a solid team otherwise.

So it sounds like data entry / invoice tracking is easier in Quickbooks which seems like a solid advantage. 

Sounds like a solid plan.

@Daniel Dang - Sounds like a solid deal to me.

"burden of proof on you"  I would say without evidence from an engineer and a surveyor that the city trusts AND Planning Desk you have no chance of overturning.