Since you missed the 2 out of 5 rule, capital gains taxes might take a chunk of your profits, so consulting a CPA would be smart to understand how much you’d actually keep.

In either case, the longer a property remains on the market, the more motivated the seller often becomes to offload it.Savvy buyers understand this and often target properties that have been listed for three months or more.

It is my understanding that gifting a property does nothing to step up basis as the capital gains would follow the gift. 

You understand some of the basic concepts, but also have some giant holes in your plan.

Thus, my main goal joining this forum is to try to gain confidence in the decision to get into real estate investment and better understand the risks that I may not be considering due to my lack of experience in the field.

I understand your frustration.

It helped me to do more research and better understand that I’d like to buy property elsewhere and rent that out, rather than renting my current property.

Truthfully, I am not that big on coaching programs BUT, I can understand the benefits of having someone in your corner teaching and coaching you on the ins and outs of real estate investing every week. 

but careful planning and documentation are essential""...making sure that your wife understands what she needs to do to document her hours and activities."

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?