With your background in architectural design, you're already ahead of the game in understanding spaces and their potential!

Your goal is to reach as many potential buyers as possible, and right off the bat you're limiting your pool of buyers.

We are looking to wholesale outside of our chosen market to help build capital for projects within our chosen market (Louisiana) as I have potential deals in other markets and am not confident in how to proceed with them contractually, (don't want to be stuck with a bill I can't handle currently and also want to ensure I'm operating correctly).

You would want to know if anything was ever built on the land (maybe a house burned down) because if there was a house then you would have potentially buried septic or oil.Buying and holding a lot for the future with topographical issues is only worth it if the price is negligible IMO.

After buying this house, I partnered with others to invest in a duplex in the Wichita area.At the moment, I’m living in Tennessee, and I’m weighing two options: either selling my house and using the proceeds to buy a duplex in Overland Park or Wichita with my partners, or keeping the house for another 3 years, transferring it to our LLC, and renting out the entire property to maximize its rental potential ( $1400-$1600 ) I currently owe $200k on the property with a 6.5% interest rate, and my monthly payment is between ($1,700-$1800).

A lot of people travel with pets so charging an extra fee can make up for potential damage plus you expose your property to a broader market that can help with bookings.

Builders do this a lot to add extra potential sleeping area without having more bedrooms than septic is rated for.I have seen people put beds in the loft after closing or even close in this area to make an unofficial bedroom.Just be clear in your pictures and description and you should be fine either way.

At least this next potential home is only a single story so I cant fall as far. 

After looking into it more, I'm concerned about potential tax implications and legal issues, such as piercing the corporate veil.

You can use Airdna & other STR estimator tools to get data on potential income/vacancy based on your location and property size.