I'm thinking of cash-on-cash ROI here in the long term (I'm in a medium-appreciation environment which helps).

If you're in an area that has a lot of college students then you might want to think about ways to create the standards you need to fell comfortable with this.

I have become comfortable talking with brokers and other experts in the industry.

Plus, there's really only comfortable parking for 1 extra car. 

I don't feel comfortable building it illegally.

Some lenders may have an "overlay" or may not be comfortable with SRO rental income on a newly acquired property, but I have done transactions using SRO lease agreements.Typically speaking, if you qualified to purchase your primary residence, and you have not increased your debts or had a decrease in income, you should qualify for an investment purchase assuming you have a 25% margin on projected rental income vs the mortgage payment.

They have helped my parents retire comfortably, paid my kids way through college and been a great way to store and build wealth.

Obviously this probably means the end of your real estate investing in that area if you don’t feel comfortable with the higher loan.

If you are looking for an investment it is very helpful to know from the numbers perspective of what you are looking for, strategy, what type of areas you are looking in, condition of the property/how much work you are comfortable with, etc.

Florida is a fantastic choice with its favorable tax environment, lower cost of living, and diverse markets.