If you are just getting started here in Chicago, house hacking is the ideal situation.

So I get that "lag" almost every time, plus I deal with our corporate bank... so they always have that lag. 

Also your permitting process, type or land, grade of land, if underpinning is required will all play a factor into your cost. 

Ideally you can provide something extra or unique that you can highlight in your photos and description to stand out. 

Play dumb, ask questions, and try to gain as much info as possible before choosing a contractor. 

Fix it.We eliminate as much landscaping as possible: we take out flower beds and most decorative features, ideally, lawn mowing is the only job tenants have to do, because we know that's all we can expect from most.

You also don't need to do a traditional long term strategy, is there a draw the  area that playing host to a traveling nurse or other professional/student would be interested? 

Ideally want to break even or cash flow with the 3 tenants.

Lost in all of this has been the significant role technology now plays in listing and selling real estate.

It's unclear on how that plays into your question about taxes.