For roommates, its more rare that you can find roommates that will all qualify 3x total rent on their own so its difficult to make each tenant qualify on their own, but also riskier to accept non related roomates, but if student roommates, you can ask for a cosigner to mitigate some risk.

This is how you mitigate risk.

I feel that the upside in rent is mitigated by the costs to service the pool as well as the increase in insurance and the over looming potential liability of the pool.

But we also had a great RE agent who would go with the many lowball offers without objection.Now days it's a tough call, unless you can mitigate the cost of repairs or do it yourself as we always have done, except roofs.

But if they don't then the monthly cost of one "house meter" 's worth of heat will be much more cost effective than time spent mitigating the damage of a potential frozen or busted pipe come winter time. 

Starting out I always recommend being driving distance from home to mitigate risk, but you will also hear about success stories from investing out of state. 

And forcing appreciation with property improvements can provide additional risk mitigation.

It will be short term capital gains though hence I hope you have some strategies to mitigate the tax burden such as being a real estate professional according to the tax code, utilizing cost segregation studies, or possibly utilizing the short term rental looppole. 

I hear ya man and understand the fear, but all of your fears can also be mitigated by having adequate reserves and renting out places in a high demand area.

Instead of planning for a disaster cleanup, prepare to mitigate that risk.