-If I find, for example, two female tenants, they will almost certainly want to be paired with two other female tenants.

Little income => little taxes at 44-47% If you are just starting out with one property and you are at a lower marginal tax bracket with your other earned income {those who are "self employed" can find ourselves in such a situation from time to time - either purposefully or not}, then the above structure is overkill and not advantageous.

I have the added advantage of also holding an active real estate license that I don't actually use for much that i could possibly put to good use.

Renting means you have a monthly nut that you have to continue to cover.Now I think renting does have an advantage in a high priced area like SF.

I feel that all of this extra time will be an advantage in my real estate investing venture!

You have a lot of competition but that just means you need to take advantage of all the investor meet ups.

There are some advantages to being off title, such as limiting liability, and its a lot simpler transaction.Anyway, if your due diligence is coming up great on the contractor, and you can triple validate the ARV, then I definitely think the deal is worth some strong consideration.

Also take advantages of some more tax write offs.Can anyone offer some ideas on how I may be able to accomplish this.

While the property "in answer" is not advantageously nestled in the part of Chicago having a "pulse" (The Loop), it isn't positioned in the boon-docks, either.  

And way to use the site to your advantage.