I already have software that does my accounting, leases etc.

Is June the end of his lease?

High rent in the neighborhood is 1300, house would need 10k of work to get it to that number so the lease has been drawn up for 1100/month,Most things are new and roof is a few years old so i'm ok with this rent amount for the first year, mostly because id rather work on the stuff at my land than this house.  

I go to them frequently and always learn something!

., minor or major, you can decide whether that is worth the trouble.I would request the rental application from the tenant, the lease, and the credit report, which are standard requirements.Those info would also allow me to check out how they manage the rental tenant screening process and what kind of tenant is in the house.

The condo is already rented out with a one year lease.

On the actual lease, I would increase the rent about $750/month for the first year to account for the $9k payment and the second year it would go back to the same rate as right now. 

Also, will renting a room almost always be a sublease or a lease?

The stopping point, though, is that we can't decide if it would be more beneficial to buy and sell via a lease option, try to house hack, or get into multi-family residents?

I have been wholesaling for over a year but am brand new to the lease option idea.