This accomplishes 2 things, 1 you are gaining instant equity, 20-30% each time you complete the process.  2.

Sounds like you got a killer deal and added some instant equity...WELL DONE!

I offered them 5K relo, last month's rent free, and deposit if they move out by Dec 1st.

If someone shows up here looking for instant riches, they are going to find it no matter what saner voices say because they are going to ignore any information that rebuts or contradicts the narrative they already have in their head.

So, I call on the phone, get instant results, or I send an email and I always get an email back a few minutes later.

The downside will be I will not be able to pull initial investment out for five years and my IRA deposit will not lower my AGI (if I am over income limits).Any additional input?

It also usually requires opening a special bank account and depositing the rent and/or getting court approval.No rent = eviction notice. 

Or if we start taking direct bookings, we can get a deposit or have a card on file to cover damages that they cause. 

You should be able to recover those charges from your last tenant's security deposit.

They came in with a dog, told us about the dog, paid a deposit and fee for the dog.We were over there for a problem recently and noticed two things.