The main point is to find distressed properties to get the biggest discount possible.

I am starting a new job and as one of the benefits, the company will match dollar for dollar up to 3% into an IRA. 

Hiring a lawyer will cost you more, but you will (hopefully) get the benefit of their knowledge and experience and then you can learn from that knowledge and experience.

This reduces the overall transactional cost and benefits the buyer.

I can see some benefit but also some downsides to it as well. 

I feel kind of 'weird' about pursuing opportunities in both areas which could divide our focus and could mean that if we find a deal in one market, our agent in the other market would not get the benefits.- Is there any etiquette here or am I being overly sensitive?

Better to build your own equity through the debt pay down, enjoy the tax benefits of ownership, and garner the equity of an appreciating asset.

I think that area is going to do well with the new complex’s going in at 5th and Main. 

Yes, people are still using Airbnb but if you are basing your main long term investment around it I would really consider other exit strategies and alternative monetization

It will familiarize you with the basic terminology and benefits.