.- Windows are oigional with old aluminum storm windows some are broken.4700 W 20th stMarket rate (conservative est) Market ratePainted, StainlessAll rentedcompetitivly priced including basement1st floor Front 2bd 1ba includes front porch9009009001st floor 2bd 1ba with heated sunroom 6'11"x 11'9009009002nd floor 2bd 1ba + front porchKitchen needs floor sanded, cabinets plaster, paintBath needs toilet & vanityPorch needs drainage8758752nt floor 2bed, 1 bath heated sunroom 6'11"x 11'900900900Basement STUDIOEgress windowsdrywall, 1 wall needs fixing500Garage$120$150$150Mortgage 260 for 3 units270 for 4 units280 for 5 units-$1,248-$1,296-$1,344heat (heat & cooking)-350-350-350Tax-$635-$635-$635Water & Garb-300-300-300Insurance-$145-$145-$162ElectenanttenanttenantUnits Rented3 units4 units 5 unitsMonthly Cashflow$142$999$1,434If this were 2016, I know I would be overpaying.

What if they are hermits who only go out once a year, drive beat up cars and cook every food at home?

If the prospective tenants are smokers, the landlord does not want to allow any smoking in the apartment.

@Ethan Cooke  thank you   and thank you to the rest who responded.as I am sitting here drinking my coffee I am thinking its probably not fair to the neighbors to do super short term rentals I have seen houses trashed by parties and my house has far to many nice things to even remotely risk that one.So probably either not rent it and leave it vacant or if I do take a 6 month lease at a time with a very well qualified NON smoking no animals tenant with a large deposit..

However, my girlfriend and I decided to upgrade few aspects (namely kitchen since she loves cooking) of the front house since we were going to live in it for the next few years.

Just moved, just started restaurant line cook job.

That's cooking with gasoline. 

They cooked for us on a regular basis and one of them helped my spouse successfully change to a much more lucrative career and they even developed a professional working relationship.

Chicago (Cook and DuPage) has been getting crushed with property taxes due to poor government management.  

Allen Cook Brentwood NH