I’m currently in the research phase for obtaining my first property, and I am looking to gain insight on market trends, investment strategies, and project management.

Why on gods green earth if you can save on commission, gain experience, meet investors and manage your own properties would you want to invest in a market outside of where you are?

When you want to exchange to a more passive NNN property. 

These expenses can create a paper loss, which may offset other passive income or carry forward to future years.If you qualify for Real Estate Professional Status (REPS) or actively manage a Short-Term Rental (STR), the losses can be applied against your active W-2 or business income, reducing your overall tax liability.

Thoughts and suggestions or too complex and take the hit on capital gains tax as I sell my rentals?

@Kyle Cross, correct me if I'm wrong, but I think maybe what you're getting at is potentially pitching to your parents that you would like to take a shot at personally managing the units to gain experience and some form of compensation.

I'm going to take them and turn them into a nearly passive fully operational business including direct booking website, OTA listings, PMS, integrated service providers, etc.

Understand that high returns mean high risk in any PASSIVE investment.  4.

What I do gain is being able to place tenants much faster than my competitors who simply follow a mold. 

It's low risk and tax free on the gain.