That would definitely affect your ability to rent during the winter, if the winters continue to be mild.  

I know how busy this will be, which is why ideally once we have 3-4 properties, the maintenance of the website, advertising, and property management will become my full time job (my wife will continue to work to provide some steady income during the transition)For your 4 questions - those are all excellent things to look out for and they are things I would not have thought to ask.

I hired a PM because I didn't want to be a PMLikewise I hired an ops manager a few years ago to deal with my property managers and other staff so I could continue to do what I do best which is be an investor.

Very excited to continue to dive into this line of asset collection and hopefully build a great portfolio for myself!

I've recently started an eviction on a S8 tenant of mine in Detroit.The process will be identical to a normal, cash paying tenant with one big exception.The housing authority will continue to pay the voucher amount during the eviction process. 

I completely agree with @JD Martin, once roots get in the line they will continue too.  

Before we entered into the JV, I outlined my strategy, which was to continue investing at the completion of every project with hopes of a new JV every 3-4 months. 

I will definitely continue to do my due diligence and get as much information as I can about Florida in general.

It is true that your investment continues to accrew interest throughout the bankruptcy process but the process can become so convoluted that in the end you will have to spend more time and money to secure a clear title than the property is worth.  

The sadest part about these frivilious law suits and/or claims is that the insurance comapnies almost always give them something, this is why they continue to do this