There are two items that you need to completely solve this problem for your rehabs: properly built Design Boards and a Finish Schedule.

TIC in this case is virtually synonymous with coop.finance items- There are several ways to finance TICs – group loans and fractional loans are the most common. - Fractional TIC loan: you can now own a unit in a building that isn’t classified as a condominium, yet from a financing perspective, will feel that way.

I would simply hire a good civil that has done development in that jurisdiction and pay for a feasibility study and let them run through all the check items.. but thats really just the start.. also for context .. these projects require 350 to 750k in CASH up front to get to approved plat status ..

Not a singe mail item sent yet.

I think you will definitely want to talk to your lawyer because there may be items linked to this transaction you are not considering. 

I will always look at the air handler and make sure tenants are installing fresh filters (most neglect this item).  

Key items to rehab on the second home to bring the property value up for the refi, determining which lenders/servicing companies will be favorable, Identifying good properties to invest in altogether.

Would you have any recommendations, in your experience, for what to look out for in the documents that would be red flags or items that would negotiable?

This strategy would preserve more of your equity and make reinvestment more efficient.You could use the exchange to buy multiple properties in diverse, high-yield markets, achieving your goal of increased cash flow.Reassess the Property’s Cash Flow:Before selling, explore ways to improve the cash flow on your current property.

Make sure to go through their estimates carefully as they may include some items that are not needed (e.g.: they added cost to board up fireplace but the house doesn't have one)- Make sure to verify if all the work is complete as agreed.