We booked a couple people so far, with one person interested in creating a mid term lease.

I have talked to OOS investors that lost big doing single family turnkey rentals in recent years because the "great tenant" that came with the house moved out mid lease and did $30k of damage on exit.What I believe you are really going after is: don't be dumb money.  

I'm having trouble finding a tenant that I feel comfortable leasing the space to.

You can always raise it again in 12 months on their next lease. 

A strategy we use is to offer to buy and close now and lease it back to them for free.

At lease in my experience that's how it should go down.  

When there's tenants already occupying the property, there's often times different leases that were signed among the tenants.Additionally, renting by room usually sees higher tenant turnover which in turn causes more work for the PM.Other challenges to consider:- Disputes/conflicts among tenants (different personalities if a tenant doesn't know the others prior)- Occupancy limits- Splitting utilities (what if someone uses more water?)

That's for tenant turns, unexpectedly long lease times.

From beginning to finish, this project took us 16 months and were 100% leased within 30 days.

A factor I am frequently discussing with clients is the nature of our current market shifts in Texas.