Putting that kind of expectation and blame on Nat for being a victim here is unreasonable and irresponsible.Nat, always check with a Florida lawyer. 

(B) If the landlord makes an entry in violation of division (A)(8) of this section, makes a lawful entry in an unreasonable manner, or makes repeated demands for entry otherwise lawful that have the effect of harassing the tenant, the tenant may recover actual damages resulting from the entry or demands, obtain injunctive relief to prevent the recurrence of the conduct, and obtain a judgment for reasonable attorney's fees, or may terminate the rental agreement.

It would be unreasonable to believe you're going to quit your job off of 15 properties leveraged @80% bringing in $200/door.

As for the heat, as mentioned above you should have addressed the heating situation on the front end; it's unreasonable to expect one tenant to control the heating/cooling for 3 other tenants in separate units. 

My first flip was a flop and I made 4k - essentially nothing and spent 1.5 years of headaches and TONS of time.I'm on my second flip which I hope to make some money next spring, praying Fed doesn't hike between then again and destroy the market.I really like the 70% rule but it's unreasonable these days unless you're talking about high end illiquid markets, 15% is more realistic.

I think one mistake that many investors make is just taking the lowest bid --- even if they should've known that the bid was unreasonable.

I’m concerned about unreasonable personalities that will either be very demanding or overly messy/loud/ect. 

Whether it is at 6 months or 1 year, tenants will move when you raise rent to unreasonable levels. 

If so, $100K per year is not unreasonable.

It was not unreasonable for you to request that it be cleaned out on your final walkthrough because the assumption is that it would've been done already!