If you are going to purchase a parcel where the seller will then build, you should take the time to ensure everything is in order prior to settlement on the land. 

I looked at potential leads in an area, but Ivelo  states motivated sellers. 

But, can definitely depend on your local market.With the market so strong for the sellers/landlords, what you see being advertised is what did NOT move. 

So it seems to me your two questions can be answered without any need to involve seller. 

Would you recommend making the sale contingent on the tenant leaving at the end of 90 days (or the seller getting tenant out sooner (eg cash for keys), and returning the unit broom ready, OR in the interest of moving forward would you negotiate a holdback in case eviction is necessary and to cover paint, repairs from wear and tear and carpet replacement, cleaning etc?

One very powerful tool is it shows how many inquires there are for certain dates so you can anticipate a high demand time frame.

In reviewing our 2023 production at least 1/4 of all our STR (particularly luxury STR) and multi family sales were the result of 1031X transactions in which the seller sold a like kind property towards a high cash flow vacation rental. 

Airbnb is a million hosts away from matching up with the current demand of people needing short term rentals when traveling. 

More often than not, those weeks would be taken during peak demand times as that's when everyone wants to be traveling to the area. 

This post delves into the key components of Raleigh's market as of 2024, including real estate dynamics, employment trends, industry growth, and the overall economic outlook.Real Estate MarketThe Raleigh area has historically been known for its robust real estate market, driven by continuous population growth and a strong demand for housing.