Since the future tenant will not be in the state until later in the month and will not take possession until then, it makes sense to do it all at the same time.  

He is planning on leaving at the end of May either way though because a 3br is too much for him to carry on his own.The crux of my question is do Isacrifice the earlier close for less risk/hassle in dealing with the current tenanttry to work out a deal with the tenant to allow me to take possession earlier but still allows him to stay until the end of May as he has planned?  

When you finally take possession give them your contact information for emergencies and let them know your planning on a walk thru in the next week.

These were extreme hoarder homes with the seller in possession after I closed and I had to evict.. and or one I had to sue for specific performance and that took 2 years then another 6 months and I finally had a sherrif lock out.. and all their possesions were there and the sherrif locked it up..

If they don't remove it, you can throw it out and you are protected.Alabama has extended redemption rights that are tied to when the investor takes possession of the property, not the tax sale date.  

When we took possession, the apartment had been vacated except for the large amount of trash they left behind, and the fridge full of rotten food, so be prepared for that type of scenario, but in our case having the seller handle it rather than restart the process once we closed was the way to go!

Control the property with a simple contract of sale, right of possession and right to market the property and assignment rights and delayed settlement techniques, make sure you put a clause in the skinny contract of sale that lets you out if you can't assign the building.Schedule a public auction. 

Two siblings living in the house out of 8 total siblings could have very easily led to years of lawsuits while your money is tied up in a house you don't have in your possession.  

If so should we commit to providing a certain time period they would take possession when we take deposit? 

If your tenant believes that and stays in possession, you will either have to wait 30 days for them to move out, or file an eviction lawsuit and possibly wait longer than 30 days if everything does not happen as quickly as it possibly can.