Finding out what market rents are in the area will quickly reveal if retaining the property as a rental even makes sense. 

Density is your friend, but seek out how to best do it to create a desirable place, minimize you utility/road costs, and retain value throughout the development stages (if phased).  

I believe disclosures / marketing materials / compliance etc it’s recommended not to be licensed.

I've retained a team to help me handle tax structuring. 

I’d need to borrow about 50% of the value of my current home to fund the remainder of the price of the new home, and would retain the current home as a rental.

I made some elections about grouping by not grouping as I expanded and didn't understand the consequences (making material participation easier/when passive losses can be harvested/ease of filing) of that at the time.Also random question but do you have a sister Nicole?

Please keep in mind, you may qualify for the 750 hour test for real estate professionals, but need to materially participate in the rental activities as well for it to be considered active (and take the active losses). 

If it is anything like ours it says that the sellers and/or agents know of no material defects.

If I "share the deal" yes I make less on that 1 deal, but I retain Bandwidth for more volume, to act upon more opportunities.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.