My joy is that you have learnt your lessons and hopefully, you will not cross this bridge twice.For me, I am not a builder, and I dont rehab....I do not have comparative advantage and the skills to do that..I will rather leave that for the experts.... my time is too precious for me to spend lifting bricks......more over, it becomes another JOB for me.....I rather take a low return with peace of mind while watching my son play basketball games that sweat through 25%.

While you may think your expected cash flow is conservative, I'd take another look at the prior owner occupied unit, it is probably in better condition requiring less maintenance in the near future, an assumption, rarely are different units apples to apples in reality. 

I appreciate the information.The house I'm renovating now needs a face lift just about entirely throughout the house, but there are no major projects or damages.  

They were short about 300SQ Ft of what is on my street.So would you say they wont consider something if its not apples to apples?

For example in the kitchen, everything is one level gray, so you might want to add color on the countertops, whether its through some natural items of small natural woven baskets, cutting board or bowls of fruits(oranges or green apples are always a good choice) or maybe adding a color keurig. 

For the easiest way is to hire an Home Inspector that will go over all points for you will cost you about $300.For the Cheapest way and best way (recommended, so you can learn from your own experience) to go down your self for a couple of hours and inspect every corner of the house, wright down all that needs to be fixed, and get estimate from at least 3 different contractors, (usually give free estimates).Very important you should provide the list to be done so you can compare apples to apples.

I'm not willing to sell my condo right now as it is in a prime location, (near Apple HQ) and I wouldn't get much cash in the end after cap gains.How would a savvy investor make this land deal work?

The only reason I can't install them myself is because I don't possess the arm strength to lift it.

I would get multiple bids and make sure you are comparing apples to apples on the actual siding. 

if the purchase price of an investment property is derived from:sales price less repair cost, holding cost, overhead and profit; the purchase price of subcontract services can be described in a similar fashion:Painting revenue less direct costs, overhead and profit.you see, we can all talk about how much we pay for trades, but until you see the rest of the numbers you're really not comparing apples to apples anyways.new question: how much did you or can you charge for the painting work that your painters are performing?