One way to get tax benefits while you're living there could be installing solar panels or upgrading the energy efficiency of the home. 

Initially, the properties that I buy in another market don't have to cash flow a lot, my metric is $150, as I'm focused on the long term gain when they're paid off  and I have a W2 and am also a realtor.

All the other fancy ways people try and get creative with owning something typically only costs you money and provides zero benefit. 

I would benefit from this program because it would decrease my 1:30-2 hours commute down to under 30 minutes.

Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

Thanks for the info I would definitely like to gain some knowledge.  

This is a two-way interview, so have a short list of questions to ask the mentor (What books do you recommend I read to gain a better understanding?

This platform is designed to greatly assist you in networking and gaining knowledge about real estate.

I shifted from investing with a cash flow focus to the appreciation and tax benefits side of things.

As an out of town owner, one benefit of Madison is that we do have a good supply of property management companies to consider.