This is what YOUR insurance is for, so that you don't have to pay out of pocket, now whether you have insurance or what type and if it covers this situation that is completely on you. 3) Another Problem Tenant: "Once repairs were completed, Evernest vetted and placed a new tenant, who refused to pay rent and caused an additional $5,000 in damages."

In addition, it's best to be close to a beach access point. better Proximity with an older home could do better than a new construction home built at the end of the street close to highway 98. 

He placed the unit on the MLS' 30 days prior to the lease expiring + 30 additional days before we found the new tenant.

Additionally, others are targeting the same lists, so finding an exclusive, highly motivated list is difficult.

If anyone could give me any additional info about the market.

So, I do agree with hedging your bets and serving a notice to pay or quit.The issue with them not paying rent and you using the security deposit is that they have zero incentive to clean the unit and if they damage it, you have no additional funds.If it were me, I'd serve them an eviction notice and then mark them as owing on a credit reporting site(I use Front Lobby).

After talking to support (who were actually quite responsive and helpful), they told me I had to publish the ad with only one photo first and then re-post the ad with additional photos later to force the first photo to be first.

There are a lot of other things you do for temporary health care travelers but in your situation that is the one additional thing I could see as being useful with a brand new health care location.   

There are additional benefits to the seller, too, as they are receiving interest on the payment and there are some tax benefits as well (I'm not an accountant!).  

You should however, (if you didn't promise to paint) allow this and other future tenants to paint themselves, in which they are responsible for the costs of painting in addition to the cost of fixing any issues due to improper paint why?