Should I hire a homeless man to scream at all hours of the night?

The most important thing one can do is buy a screaming deal with minimal surprises and low-risk.

Background info: A+ area (wicker park), 3 large 3 bed legal units, 1 non conforming, 5 minute walk to El, quiet desirable tree lined street, huge ceilings, tons of light, original millworkCurrent Rents: $7220 (3x $2000 + $950 accessory unit + 250 garage)Price: Under contract for 1M, expecting about 30k in buyer concessions (nothing major, but seller indicated flexibility to address anything)Pros: 40 year owner, new roof, new windows, new garage, recent boiler/water heater - stout mechanicals, easy to duplex down into basement to make 4bed / 2bath 2250 square foot unitCons: window AC, radiator heating (3 separate meters, but one tied to boiler - owner covers heat), single coin op laundry, porch in usable but older shape, older kitchensComps: $1.15-1.25M for similar but upgraded rental (not condo standard) units.Option A: Do nothing:If I were to do nothing at all and keep rents (below market atm - at 20% down (interest rate is unfortunately very high, but such is the time - 5%) with 4% loaded for fees, $200/month for radiator gas in entire building, it's cash flow $0, CoC $0.Now of course you might be screaming this is a terrible deal - I think there's a lot of value add here for a unique building in a prime area. 

In my brief analysis of the Dayton area single family home market, I don't see any way (short of getting a super screaming deal) of getting much greater than 1% (rent/appraised value) other than in West Dayton area.  

Mandel & Ogden will lease up their units then move to the next big headline, but the mom & pop retail shop that poured $100k into a new facade, logo, image or equipment are screaming loud and clear they are there for the foreseeable future. 

Well, we have 3 short term rentals - our basement in Denver and 2 condos in Breckenridge - all in great locations for visitors. 

Any market that has a lot of visitors can potentially be a good STR market.

I'm also not seeing screaming flip opportunities in these neighborhoods.

It's unlikely that this would happen often, but if someone did heavy damage it would be worth it.Additionally, the renters liability portion would also be another layer of protection between visitors and guests and the landlord.

During the last recession, there were over 9 million ANNUAL park visitors between 2006-2010.