The goal is to use post-tax dollars in order to avoid paying taxes on the gains.2.

Many of them don't have a lot of cash reserves if they're paying high mortgage, rent, have children etc. 

Presuming you are somewhat real estate savvy you can list it on MLS yourself and avoid giving up the seller’s commission you would pay with an agent.  

those who are looking for a move in 2 weeks ahead of time are those who haven't found a place yet or people who have to move (eg being kicked out of their old place for not paying rent).  

Are you all still including this coverage (Wind/Hail/Storm) and paying the premium for it or are you buying policies without Wind coverage?

To really reap the benefits of your ownership of the NY property over the years you'll want to sell and do a 1031 exchange whilch will allow you to reposition your real estate anywhere in the country and into any type of investment real estate --- without having to pay tax on the profit from your sale or the recapture of depreciation. 

If the new people want the unit prior to the end of the current tenant's lease, I would tell them they would have to pay the daily rent beginning the day they got the key and took possession.

What property management software you guys are using, and how much are you paying for it?

Unique fact pattern with an unreleased deed of trust. 

@Shervin Golgiri Seller not paying buyers agent commission wont have any bearing on finding qualified buyers in a sellers market .