Example if an asphalt roof lasts 20 years and has a cost of $10K, then the estimated cost associated with the roof is $500/year (this is likely a little high, but I wanted to use simple numbers).  

It might mean you pay more for architectural shingles today instead of putting the 3rd layer of asphalt shingles on.

.#3 Contact Local Contractors for Labor PricingCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

I had a similar situation on one of my deals, only it was disclosed up front that the building final inspection had never been ordered, and also that the fire marshal would not sign off until a concrete or asphalt drive was put in.

@Michael Hayworth And I have heard that permitting is not a big deal in Texas, of course, I am not from there nor I have ever done any business there, from what I've heard, they only want mechanical and electrical done correctly, never heard of any asphalt shingle roof repair needing permits, nor interior walls, or hanging cabinets, alas, CA does, I mean, what's the worse that could happen on an improperly installed roof?

Asphalt shingle roof average lifespan is maybe 20 years. 

Which can be a major relief for them and can lift a huge burden from them.For investor buyers - they do all the grunt work pounding the pavement, marketing and talking to potential sellers in precarious positions and work out a great win win cash price that allows room for an investor to get a great deal on their buy and has room for a fee for the wholealers efforts.

This would be some serious wiggle room for not only moving back to Chicago, finding a job, but then start hitting the pavement on purchasing.

There is no landscaping fortunately (asphalt parking, no lawn or garden), I was assuming though that the snow removal would be included in the maintenance since I tried to apply the 50% rule here.

I like a great deal as much as the next person, but realistically, if I'm long distance, it's going to be harder to find something if I'm not out pounding the pavement locally, so I figure I'll probably be more reliant on what's on the MLS and wholesalers.