@Sandra Pinzon I think most land lords in Chicago include the heat (gas) if you have a central boiler.

My question is: Does it matter how I heat the back porch?

On Thanksgiving, the boiler ignition switch required replacement, and as they were away, I went over to ensure it was done so they would have heat when they got home.

All the while you’re discounting the tenants rent or paying for them to stay in a hotel if it’s hot water or ac or heat until you use someone else that can fix it the same day. 

Rents would be 2000+2650(util inc)+1200=5850I owe about 360k on the Mtg in NYNY Expenses: Mtg-1700, Taxes-650, Ins-200,Heating Oil-200, Cable/Internet-150, Water-200, ConEd-500, Landscape-150, Supplies-100 = Total of 3850 Leaves me with +/-2000 in profit.. and realistically , after the Tampa mortgage payment is made, I have $400 left over every month.

That being said, you are also going to have to deal with 3x the tenants, and 3x the expenses in some cases (3 roofs, 3 heating systems, etc).Not a tax professional, but pretty sure you can write off the mortgage interest you pay, which is another benefit to getting a mortgage v buying in cash.

He also pays for heat for the entire building, so given the already-low rents, it's not cash flowing like it should be right now.Appreciate your response!

A management company that fixes a broken heater within 24 hours on a holiday weekend is a superstar company, when some tenants may feel a couple hours without heat is unacceptable.

Do you have electric heat then I presume?

So without doing anything I ended up with this brick 3/2 for $40k.The house wasn't the Taj Mahal - I had to put a new roof, repair the heating system, and do a lot of rehab upstairs to the tune of $25k - but in the years I've owned the house I have made over $100k in rent on it, the value of it today is in the $250k range, and after a few years I pulled a BRRRR on it and got all of my original money back out of it.