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.

When it's time to sell, you can use a 1031 exchange to avoid paying capital gains on the sale.

It will familiarize you with the basic terminology and benefits.

The flexibility of the HELOC will benefit you more every time, and although your spreadsheet might night reflect it, in real life, that flexibility will almost certainly result in lower cost to you over the life of the loan.

I look forward to continuing to gain knowledge through this forum and hopefully giving some back.I have started searching for properties and putting in offers through a Real Estate agent I trust. 

The upgrade benefits the tenant directly, but also yourself by improving the asset you own.