I've heard that the Sarasota County is in need of money (and that's the reason AirBNB deducts taxes and directly passes them to the County) - how strictly are those rules enforced? 

Is the tenant responsible for all interior and exterior pest problems or is it strictly interior?

It's also essential to understand local regulations regarding short-term rentals, as they can be strict.

Great input, @Greg Scott and thanks for linking those articles.I honestly hadn't even considered HELOC interest deductions, and it's not surprising that the IRS & banks have strict guidelines around this to protect themselves. 

Start up cost have strict rules too.

I am very strict when it comes to smoking. 

Am I being too strict?

Be cautious of cities that aren't proactive in job attraction; too much growth can lead to strict building regulations, affecting housing value.Other Factors- Favor cities with a crime index that has consistently decreased over a decade.- For appreciation, I look for a minimum of 2.5% YoY growth in median house values over the past 20 years but I don't use this explicitly in calculations.

The Heights belt I am referencing is strictly the more South/Southeast area (Garfield, Maple, Warrensville Heights)You can definitely find some solid multifamily in the Shaker Heights area.

Renovated all apartments, converted M2M tenants to annual leases, instituted strict rental criteria, implemented online payment portal, invested $75,000 into leasehold improvements (HVAC, drainage, exterior paint, concrete.)