Here's my perspective as a lender:You are in the right place to start researching.

If the property is on the border of Logan Square you usually cannot use a recently sold comparable in Hermosa.Now you can use the NOI to promote how good the property is from a cash flow perspective but appraisers generally won't use that number to determine the value.

This direct booking website doesn't cost any more to operate.I'm not trying to be snarky @Dave Stokley because I have had that same attitude for the last several years myself, but seriously, from your perspective, having all eggs in the Airbnb basket, do you just feel like the risk is not there or do you have other backup plans if you were to be shut down, due to a bad guests and airbnb taking their side for whatever reason?

I posted my rental ad on multiple platforms (zillow, trulia, zumper, craigslist, apartments.com) and set the rate about 10% higher than the market with the intention to lower it gradually and also my unit is freshly renovated and nicer than the comps.

From a fair housing perspective, you should have written tenant evaluation criteria.

If you have $25K to put to use, best to use it on kitchen/bathroom remodels, landscaping, fresh paint, hardwood or similar floors instead of carpet, etc.

We were able to come in with fresh eyes and made the house look pretty again!!!

Full bathroom remodel, new flooring throughout and fresh paint. 

@Filipe PereiraThanks for sharing your perspective.

Remind the tenant that she obviously has not been happy there for quite some time as evidenced by the problems she has had with other tenants - and that this is her opportunity for a fresh start.