I think it also works best when you book closer to your arrival date. 

You may have the bedroom count, but sqft is very low for that rent, your probably closer to $1700-1800 than over $2000 in that area, maybe north of 210 Shandon Hills, maybe the Del Rosa/Sterling area, San Grogonia area, close to Highland or casino area might get closer to those rents.It looks like your trying to Finance with an FHA loan, watch out for mortgage fraud, SB has been a hotbed of mortgage fraud in the past and it is much more of an issue today than in the past, not saying they are looking to lock people up but occupancy fraud is one of the most common forms of fraud and lenders do look for it.

Anything you do that increases the footprint of a residential structure requires substantial permitting, and inspections. 

They will also charge you to have an inspection by a 3rd party to make sure the work is done.

In addition, a termite inspection and home inspection is a condition of the sale.

I guess it truly comes down to if I live with my roommmates in a home closer to downtown (which I would enjoy as well); I would have more control of the tenants as they are my college roommates and long time friends.  

Perhaps if you wanted to do an occasional meet-up somewhere closer to my area I could attend.

We did not ask but they invested almost 15k after we wrote the offer to get it to pass inspection.

You might adjust depending on what comes up in the inspection, of course :)I wouldn't base your investment decisions on Rentometer.

If you really are going to get rents closer to 30k, you'll be at roughly 8k/yr or roughly $100/door per month.