But if the lease terms are murky, if renewal conditions aren’t guarenteed, or if the airport authority could dramatically shift the deal down the line, then you should be asking for a discount..or at least some protective clauses in the contract.I’m curious... if you were to step into this kind of leasehold now, how do you think you’d explain the upside to your future buyers or partners when you eventually decide to exit?

The best and most appropriate way to get a value, in my opinion, would be to use a discounted cash flow model.  

cash flow has just been hit hard everywhere with the rise in interest rates. the properties in my portfolio that cash flow the most are at interest rates that it's not possible to get anymore - low 4s - and somehow there is still tremendous demand for properties that won't cash flow or break even, which is what you're finding.based on what you've said about your current situation... i don't have a good answer for you. 

The potential here is tremendous in many different ways.

Listing immediately at a bit of a discount to fill it quick on ST leases to reup in spring.

Sounds like you have a nice cash flowing property already and see a tremendous opportunity with a new property.

I used a property manager (before I was one) for (1) time & headache savings and (2) the value the property managers provide by economies of scale (marketing, discounts with vendors, etc.).

If you don't know how deep the water is, you may get more than just your "feet wet".Third Lesson.Cheap and discount are not the same thing. 

Strategic Purchase: Acquired a discounted double lot below market value with a $17k impact fee credit.Custom Design: Built a 6-bed, 5-bath home tailored for co-living or multi-gen use, maximizing tenant appeal.Efficient Management: Managed construction, and self-managed operations to minimize costs.Premium Marketing: Furnished the property and used multiple platforms to attract quality tenants quickly, achieving full occupancy.What was the outcome?

Because there have been such significant gains in the markets this year (unless you are a bond investor😬) fund/asset managers and stock traders will likely do some portfolio rebalancing in January, selling winners, and locking in tremendous 2024 gains.