Any expenses you have driving there, ect you can deduct mileage for expenses on your taxes.Mom gets to claim the utilities, insurance, property taxes, depreciation, and your wages, and any costs for repair and upkeep as expenses as a deduction on her taxes from the 1st day it's rented, Any repairs / expenses prior to renting it out the first time is not deductible. 

If the market rents don't cover the cost of the upkeep of the building, the property manager will have a hard time explaining the income statement every month - because there won't be an income.

Only one has purchased two vacation homes and has left them with no maintenance or upkeep for the last thirty years.

This will give you an idea of how much you'll need to put in and upkeep for the long term.

Since the signs are always on my car, can I write off everything such as all milage and expenses related to the upkeep of the car as a travel expense or am I still required to keep personal millage and business milage on a milage log separately and am only allowed to take the standard millage deduction? 

I would think the license upkeep and MLS dues would wipe out any commissions you'd make.

I own a 5 unit and even for that, they weight the comparable sales approach more than income approach.  

This is what I was reading..For passenger vehicles, trucks, and vans (not meeting the guidelines below), that are used more than 50% in a qualified business use, the total deduction for depreciation including both the Section 179 expense deduction as well as Bonus Depreciation is limited to $11,060 for cars and $11,160 for trucks and vans.Exceptions include the following vehicles: Ambulance or hearse used specifically in your business;Taxis, transport vans, and other vehicles used to specifically transport people or property for hire;Qualified non-personal use vehicles specifically modified for business (i.e. van without seating behind driver, permanent shelving installed, and exterior painted with company’s name).Limits for SUVs or Crossover Vehicles with GVWR above 6,000lbsCertain vehicles (with a gross vehicle weight rating above 6,000 lbs but no more than 14,000 lbs) qualify for expensing up to $25,000 if the vehicle is financed and placed in service prior to December 31 and meet other conditions.

Regarding the other market variables, how does one rationally decide how to weight each variable if one simply has the goal of highest long term IRR for SFH Buy and hold strategy?

People tend to think of a CPA as just an added cost, but a good CPA is worth their weight in gold and makes you much more money than they cost.