Plot 1: 2024 market value of $6,900. 45x120Plot 2: 2024 market value of $3,800. 100x94I'm still pretty new to the game, so I have no experience with land deals, ground up construction, zoning, things of that nature, and am wondering what the best play is.Sell one to help with acquisition costs and build an ADU on the other?

I was thinking of starting a rent increase for my 1 bedroom tenant voucher due it being low and well under fair market value(Based on  hud and zip code) but my tenant is in the process of having a caretaker for her disability and getting approved for a two bedroom voucher.

How feasible would it be to transition her to Section 8, and how long could this process take in Brooklyn, NY? 

I've never heard of this.I suspect he's using fraudulent documentation.Stick to your process.

Once you have a PM put it on market for rent your friend is more then welcome to go through the process with them.

Most real estate agents actually do not have the need to go into an office to close transactions and meet clients at either a natural location or at the properties they are showing or listing. 

It just makes the whole process smoother and less stressful.What’s your experience been like?

Quote from @Rene Hosman: @Austin Wolff recently went through this process of identifying markets to purchase in and he goes over his thought process in this episode on the Rookie podcast about how he used the MarketFinder here on BiggerPockets to find markets that met his criteria Podcast: https://www.biggerpockets.com/blog/rookie-473MarketFinder: https://www.biggerpockets.com/marketsI specifically only focused on 2 markets (Indianapolis and Fayetteville, AR) before I found a deal using the BP "deal finder."

Choose the one that offers the best deal and service, and you'll be set to move forward with the process.

Anytime you are looking at purchasing a condo with a mortgage, the HOA Questionnaire is always going to be a key point of the loan process.