@Alec Jacobs it’s been a few years but when we did it, we got a ridiculous range of pricing so definitely get more estimates.

With CAP rate take the annual rental income (of all 5 homes) annualized with the home #1 at estimated $1000 per month gets you $64500 per year gross income. 

Finally, If I'm living in the 3rd unit and plan to move out upon purchase of a new property, can they estimate the income of the 3rd unit will provide with me moving out and apply that to the property's sustainability?

Just trying to rough estimate total rehab costs before putting in an offer!

Using a contractor contact the rough estimate of work required is 20-25K.   

Conventional lending has 2 reasons they want a borrowers loan to be ___% less than estimated market value.

Just put income from your last job and put an estimate of what you will make in youre new job.

Is there a website that I can get an estimate on the re-hab price of xyz location?

Because the Adjuster's fee is normally a % of your claim payment, you may want to get estimates of the rebuilding costs and see how close the proposed settlement is before you decide if the Adjuster is worthwhile.  

FHA will also not loan on the house mentioned above because they estimate that the repairs could be in excess of $5000.