They leave when they choose regardless of a lease.

Now that it’s getting close to the time for me to leave, I’m rethinking my strategy.

You should never leave your client alone in the seller's home with the home inspector.

If I had a tenant I didn't want to stay, I'd have to either evict them or hope they wanted to leave on their own or pay them up to $4500 to leave (that is another topic altogether). 

@Karen Lipa I would have someone remove that section out of the yard and leave it as is.

Mother-in-law= $1000/M for long term lease, or if AirBnb'ing, $1,600/M.Both of these numbers are being very conservative by listing below market in an effort to get more traffic.Our original plan was to live in mother-in-law suite and rent out main living area leaving us with a monthly mortgage of roughly $700/M.

If instead I leave the property paid for, the free cash flow is $1279 mo.With these free cash flows, it would take 5.9 houses with a 20 year note each, to equal the cash flow of one paid for house.

Because I have spotty job history (Mainly internships since leaving the military), securing a loan to own a property is out of the question.

personally I would pay off my home first. that would still leave you plenty to invest. it would provide more security because your home is free and clear. 

This is what my direct mail campaigning schedule looks like:Week 1: Send out your mail to your listWeek 1: (Optional) Start targeting your prospects with online adsWeek 2: Call up all your prospects to follow up the mailWeek 3: Send text messages to all the prospectsWeek 4: Leave voicemails (whenever possible)Week 5: Send out the second batch of direct mailHope this helps.