@Joel Arndt Entering a new market is always going to be time consuming, hard work and carry inherent risk.

Depends are who can crunch the numbers better, depends on who is willing to take bigger risks, depends on who is hungry for it, depends who has better cash upfront, depends on who has better credit. 

Some people like that because it means I'm taking the risk and they don't mind paying for that. 

If you have enough funds to say, buy 4-5 houses, that's more risk to you. 

You could also do Purchase and then Sale #1 and #2 (which is what I have done) but that adds a little more risk of being able to sell in time so only advisable if your purchase was a smoking deal.I'm sure you are aware, but total sales price of #1 and #2 combined must still be less than the purchase price to avoid boot.

After reading discussion on this I now feel that I may be better off just having good insurance and doing what I can to mitigate any liability risk through good management.  

Some hard money lenders are also able to do a refi out of a flip loan or all cash purchase without the seasoning of the traditional mortgages, rental income history, or W2 income qualifications.You can also ask what problems and risk you are willing to take.

I would make sure you're knowledgeable on Maine's landlord-tenant laws regarding security deposits and the risks associated with renting to a smoker before following through with any of this.

If you give them a gift card for their inconvenience, you risk setting up an expectation that when they're inconvenienced, they get a reward.

As part of my risk avoidance/Exit strategy analysis, I was taking into account the possibility of a market correction or a deeper financial trouble around the 18 or 24 month mark.