I'm 43 years old If you have other investments that have decreased in value, you could sell those investments to offset the capital gains realized from selling the company stock.

Here in chicago LTR rents are way up since 2021 many 20-25% higher so those still work and I have not seen any decrease in demand on investment purchases. 

Assuming I purchase a house with the intent to fix and flip in a 6 month window, do the carrying costs I pay increase my cost basis, such that my taxable profit is decreased?

You can find higher ROI (on paper) here and probably in other cities…but the probability of actually collecting rent significantly decreases.

I also know in the beginning mistakes will be made but I feel with a mentor through their experiences I can decrease the mistakes being made.

Now that the lease is expiring soon ,the tenants are asking for a rent decrease because five people will move out.

Since as inventory of rental options decrease, the demand for those that effectively operate as AirBnB's should theoretically increase. 

I suspect as rates continue to decrease terms will begin to improve and more buyers will re-enter the market/ be able to pull trapped equity out of their recently completed projects.

The median sale price rose to $350,000, reflecting a substantial 10.8% increase from the previous year.Total housing inventory showed a notable 19.2% increase from a year ago which is much needed.Half of the homes sold were under contract in 23 days or less, a slight increase from the previous month but a decrease from a year ago.For sellers, 43.5% of homes sold for the asking price or above, with 21.5% selling for more than the asking price.

. - December saw the largest drop in leads, the number of leads decreased 18% throughout our markets. - January experienced a significant increase in demand.