It's a 2 bedroom, 1 bathroom, 1000 square foot house, on a small lot (under 1/4 acre), and definitely needs some major updating. 

I think if you are going to evaluate price too, square footage is a good measure for how much you should pay and how much each unit should rent for.

Find out who sells the straightest lumber in your area... lot's of carpenters will not work with lumber shaped like a banana. if you understand plumb,level and square!

Neighbors want to buy it and offer $90K for it and was declined.Zillow listing for 672 sq feetThere are 2 "homes" on the property. 1) 2 bedroom and 1 bath (672 sq feet): Every window is broke, the foundation is falling apart, needs to be completely gutted and rebuilt.

Last November, very late at night, a tenant of mine broke the toilet inlet pipe, causing a flood that led to about 500 square feet of laminate flooring getting wet. 

It's a cottage about 1500 square feet and we pay about $1400 per year.

If not you can walk away.Here's a specific clause that I have used in a similar situation:------------------------------------------------Commercial Tenant/s Requirement: Buyer shall have thirty (30) days from acceptance ofthis Offer to Purchase to identify one or more qualified retail tenants for the subjectproperty or this offer shall, at Buyer’s option, be null and void, and all earnest moneyreturned to Buyer immediately.A Qualified Retail Tenant is defined as a prospective tenant who (1) has profitablyoperated a similar business to the one proposed for the retail space for at least the past 3years, (2) provides reasonable evidence that he or she can obtain or retain any necessarylicenses or permits for the proposed business, and (3) signs a Letter Of Intent to (i) rentthe ground floor retail space of the property for at least 3 yearsstarting in 2014, (ii) pay rent of at least $20 per square foot per year Triple Net in the firstyear with index-linked increases for the remaining term, and (iii) pay for any constructionor modifications required to operate the proposed business.Seller or Seller’s representative must be present during all showings to prospectivetenants

But be careful adding those stone trimmed pillars and square columns to homes not in that style, for example Colonials - because they'll really look out of place.

I have done national searches based on cheap square footage to highest rent rate ratios for multi family buildings just to see what areas come up - then evaluate from there.  

Jonathan Tea in and around Fountain Square and Bates Hendricks areas of Indianapolis.