I have been following the Real Estate Investing industry for a while and just recently decided to put my focus into it and implement a plan I had in mind for years.So I went down to Puerto Vallarta I put together a team of local realtors, brokers, contractors, property managers and a lawyer. 

Since you mentioned you're working 9-5, I’d suggest look into turnkey rental and considering property managers to help manage you’re property.

I manage almost 400 apartments in Cook County at this point.

.: I’m currently renovating a rental property and exploring ways to manage costs without compromising on quality.

Please no politics here, just looking for guidance on what may happen based on your insights so I can manage my bsusiness. 

Not a rookie - While I have never purchased a home without an agent, I have purchased two homes in the last fifteen years in Denver and, at some point, managed both with some form of rental income, plus helping my mom manage the independent basement apartment in her home.

Self-Employment Opportunities: Would it make sense to start a side business related to my rental properties (such as property management) to access more deductions?

Or hire a PM company to manage for you?

@Patrick Drury what did you think of Propertyware and Rent Manager?

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.