My top recommendation is to begin by contacting property management companies in each target area.

Because this is your first rental property, I would recommend finding an amazing PM company and paying them what they are worth.

I would suggest looking into Hemlane, I have worked with the CEO personally and they have a great product that I recommend to all self managing landlords. 

I would recommend looking for local FB investor groups, most areas have them!

It's obviously not a ton of money but how do you guys recommend me investing with it?

With a 9-5 job too busy to catch a breather, being that it will be my first rental property would you recommend finding a property management company to oversee the investment property OR create a profile on a property management platform, I am thinking about Avail unless there is a better platform, to collect rent and hire specialist as issues arise from tenants?

City Hall want to keep small town small, does nothing to promote town Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

It also depends on how you hold your properties; LLC, S Corp etc... as to what the agent will recommend.

I'm looking for neighborhood recommendations in the Sarasota area for a short/mid-term single family or townhome investment in the 400k-500k range.

If you spend the entire $300k restoring the property, then here is the end result:- deductible casualty loss of $50k- no current tax- the restored property has $0 basis and cannot be depreciated- when it is later sold, the entire sale price is taxableMechanics and reporting are tricky, and I would not recommend to DIY it, especially since my scenario is over-simplified, and your real scenario is likely to involve more gotchas.Thanks so much.