You will be judged on whether this is a reasonable accommodation if it were to go to court so tread lightly on this one. 

The advantage here is that I can invest in a smaller deal than option one, learn the process of buying real estate, and proceed to purchase a second duplex shortly after.

Then and only then would I proceed with the deal.Regardless if it is a wholesaler or not, you need to know how to obtain accurate numbers (ARV and rehab) so that your purchase price makes sense.

So that could be a benefit to the seller.If the seller is wanting to do another 1031 then they will have to do some specific things to accomplish both the 1031 and owner carry.The note, as a proceed of the sale has to go into their 1031 exchange account. 

I will make a point to ask this question to the loan officers first before proceeding with the loan.

You could 1031 the proceeds into another property but that comes with specific rules and I think 180 day timeline, if you don't meet the criteria you're paying taxes on the sale. 

My gut says leave it open and not worry about them not paying until I have to go to court and say “hey they became vindictive on me”Best, Michael

Tell the tenant to go after the previous owner for their deposit in small claims court. 

Any advice on how we should proceed? 

He proceeded to tell me about his last job that he had just lost 3 days before and the reason he lost it.