I highly recommend all renting in Philadelphia read.https://www.inquirer.com/philly/business/energy/3rd-circuit-throws-out-landlord-philadelphia-gas-works-liens-lawsuit-20180720.html

We didn't sleep one wink while our first renter was in our STR condo...I was literally scared to death worrying about everything from them not knowing how to use the Keurig to them burning the building down trying to light a candle or something!

I'll take on 1-2 of those problems (capex, management issues, or general remodeling), but won't tackle all three problems because I'm unwilling to put in the time and energy required to operate against solving them, which is why I haven't landed a deal recently...

My cash flow will still be positive with everything considered, but I would be able to turn and burn onto the next property if we go with the 5/1.

Trying to make that big jump when you have no experience is high risk for a big crash and burn, imo.

I’d burn the midnight oil educating myself and learning what I needed to so once it came to execute, I was able to do so confidently and not needing to be available at all hours of the day.

I've seen so many folks crash and burn when they outrun their supply trains of investment and decide to throw in the primary to continue their pace of investing.   

You'll have at least one or two "professional" tennants that slip by and are just there to rob you and make your life miserable.Sadly until you have 20 units and are golfing at noon on a Monday you won't be able to change your family's minds.I remember more than once having to burn my clothes along with an entire house full of stuff with my dad because it was just... gross. 

I plan to install metal roofs, energy efficient appliances, plant small pollinator gardens, and eventually install solar panels (when solar energy becomes more affordable and if my market will allow higher rent for a lower electric bill).My question is if pollinator gardens could be a liability as they attract bees and other stinging insects. 

There are conventional products that offer 3% down options so you can at least have the opportunity to burn off private mortgage insurance.