I suppose they would be able to help me figure it out but I’m still trying to determine what is the best way to fund something like this and would it be better to sell off the entire purchase once split into separate parcels or is there a way to structure a deal as to where I could sell off some of the land to repay the loan/investors and also retain a portion of it to develop with my own short term rentals.

I compared other properties in terms of age, sq ft, acres, beds, baths, basement, garage and a subjective measure of interior condition.I have a huge problem with the automated comps (Zillow, RPR, etc) because they could not account for the interior condition. 

With careful planning and consistent effort, you can create a portfolio that aligns with your long-term goals.Good luck!

This aligns well with your goal of achieving $11K/month in cash flow and retiring within 5-10 years.

You may need an independent appraisal if the value of the property exceeds $5,000, as the IRS generally requires this for non-cash donations of significant value.Capital Gains Considerations: If you've owned the property for more than a year (which you have, having owned it for 10 years), the house is considered a long-term capital asset.

We were there looking for another property that we could buy together on the beach that we could rent out as a short-term vacation rental.We we're living it up and having a fantastic time zip lining, eating delicious food, and seeing the monkeys in the wild.it seems like from the moment I returned from that trip in August 2022 the real estate market completely changed.

Everybody is different, some people like flipping, some like short term rentals, some like long term rentals. 

Does it make a difference for privacy (in terms of public records, so disregarding lawsuits)?

Both Raleigh and Greensboro have their advantages, but with your experience in Greensboro and proximity to Cone Hospital, MTR (mid-term rentals) could be a strong option, especially for traveling nurses or medical professionals.

I would rather have a good Longterm tenant under by $35.