I appreciate crime has increased in the areas recently, but I'd like to think the city will eventually address the issue. 

They escalated the issue to the national board of realty, prompting the listing agent to finally respond.

@Kiersten Vogt there is 0 chance I would gamble with what around here is a $35-40k issue.

@Ashley Baldock, I would be careful about denying people with background issues that they DON'T have!

The majority of my career has been working in NYC and I have a bunch of connections there so I don’t see an issue with getting a new job.

On the 2 long time STRs, we have made enough over the years (income in 2019 was over 1/3 the purchase price) that having an off year is not an issue.  

At the same time, if I dont buy an alternative, then I will never be able to depart with my expensive house that is a bad rental...

Are you comfortable with the sargassum issue.

I am looking for something that is user friendly, makes automated emails to tenants the day before payments are due, when they are issued a late payment fee, an eviction notice, has the best credit card processing fees and automatic payments. 

You're just trading direct-pay tenant issues for S8 issues.