I had been told that I cannot deduct mileage from my home to my rentals (I drive by weekly) as it was not from my place of business.

Please show me your bank statements to provide some amount of assurance that they have some number of months cushion so they would continue to be solvent in the case they get sick or in some way can't drive / perform the activity. 

Our attorney did not alert us to this factor which would have greatly influenced our purchase. 

I also factor the insurance, hoa dues, garbage collection, snow and lawn, utilities, advertising, maintenance/repairs, CapEx, and property management.

that was my worry about selling too soon, and the only way i can see myself breaking even would be to do a for sale by owner. i didnt factor in the benefits that might come from prospective lenders should i choose this as a rental, so this may definitely sway my decision. you are also correct in that one area i was initially looking at for properties is in Aurora.

PB&Js and driving beaters for me, but some like to remove the band-aid more slowly.Learn while you knock out the cc's.

The vehicle being my primary vehicle  is why I was thinking SUV for normal driving/REI driving since they sometimes have a 30+ MPG rating.

You are able to find deals within 2-3 hour drive of NYC.Invest long-distance(turnkey or have a team on the ground)investing in NYC itselfAre you looking to move to Miami when you find the tri/quad?

Time is a big factor when it comes to this kind of thing.

I'll be receiving a 1099 from a company to my llc for driving truck.