For example if they're in a position of financial hardship and need to sell the property asap then an all cash offer for $20k below asking may sound very enticing.

With small businesses having 12-24 months of recovery ahead, that could cause them to be in the red each month...not raise wages...i.e. people have even less money than before. ...if commercial prices go into a recession, which could cause commercial properties to sit abandoned and not be enticing for new tenants. 

The upgrades help make the properties more enticing which leads to better tenant profiles.

But the potential here is really enticing.

If you have a nice website, entice them to go there.

So the idea of paying only about 150 bucks a month per person is really enticing, but you'll get a lot of situations that I imagine are not ideal in the landowners eyes.

It was very enticing because of the low-interest-rate I'd assume along with being further into the amortization schedule (less interest more principal).

They seem to be steering everyone toward starting as a passive investor in apartment complexes (especially distressed ones) because the potential to upgrade the property and gain a fairly quick return on your money is enticing, but ... $18,000 membership with LS and a minimum of $50,000 to invest on first deal is a bit scary.  

They might be willing to sell at a discount (although typically not a large enough discount to entice an investor), but they don't want to pay an agent 6%?

In general, smaller buildings in NYC are difficult to manage as they entail a slew of services (rent collection, bookkeeping, maintenance visits, tenant disputes, leasing, local law compliance, payroll, insurance, insurance audits, etc.) that aren't cost effective for the owner of a small building, and the fees aren't enticing enough to afford the best talent in property management space.