The latter is more rewarding, as I get to use my cash right away, and possibly make my second purchase a live and flip.Our house is in great shape on the inside, but could use a fresh coat of exterior paint, a fresh layer of asphalt on the driveway, and some random things here and there.

Is it as simple as putting asphalt sealer along the base of that wall and calling it a day?

.#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 can sell it to the letter-writer and get my price, then I have to go out and pound the pavement like everyone else and try to find my next deal. 

Only asphalt shingle - I had 3 roofers show and never send an estimate....

Get quotes on some replacements for the ones that are in the worst shape.I'd personally tackle landscaping AFTER the pavement/parking issue.I highly suggest you make an Angie's List account so you can find local contractors (with reviews like Yelp) to take a look at each deferred maintenance issue you have.

.#3 Contact Local Contractors for 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.

Otherwise paint a stripe on the pavement,  and any portion of anything parked over the line gets towed. 

Make sure you understand EXACTLY what kind of roof you are getting if it's asphalt what exact shingles, underlayment synthetic or felt and ice and water shield.

Asphalt Shingle lifespan is around 10-15 years (we prefer to use lighter roofing materials and lighter materials in California for Seismic reasons) comparing to metal which is 30-45 years, much heavier product.2.