Expenses are lower, and during high season, you can raise your prices, and people are willing to pay.

Are there any challenges or reasons why some of these tenants wont be able to pay through the software that I am not aware of?

As for the leases, would you recommend keeping the tenants, potentially raising rent, and extending the lease to a long-term rental, or would you recommend finding a new tenant? 

.: I'm not aware of any requirement for this.I do provide an application because it has a lot of information necessary for tracking the individual: social security number, driver license number, previous addresses, etc.When you take over an existing renter, I recommend you figure out how to get the entire file from the former manager/landlord.

I mean, I recently raised $30 million for a single deal.

Does anyone have any ideas on how to minimize that tax liability and still continue with my original intent, or is my only option a 1031 (I'm aware of DST but don't see that as a great option).  

Make sure to the landlord is aware they will need to issue a 30/60 day notice prior to the lease expiring.

Later in the day, I was set up with a call with Peter because we raised concerns about paying $10k–$15k upfront, especially since we’re supposed to be “partners” in these deals.

I aim to generate leads and spread awareness that a property is for sale.

I am certain you are aware all areas have increase, 2, 3 ,4 times over the last 10 years, YES even PARTS of EAST CLEVELAND.