I'm paying rent now $2,000 per month, essentially throwing that money out the window.

The cause most glaringly was a window A/C unit that was placed by a licensed vendor from Edison.

. - Property 2 Missing Sidings / Rotting trim under windows (which I'll be abel to fixed)

.- Gas Boilers - 30+ Years Old- Hot Water Heaters - 10+ Years Old- Electric Panel - Upgraded within past 10 years but could be upgraded even more- Pipes are old, corroded, and some leak often- Windows/Doors that haven't been updated require much more labor to remove/replace as the wood is often rotted- Roof is old, has recent touch ups but will need a major repair down the road (10 years hopefully)- Interior is covered with old wall paper, most walls have multiple layers and are a PAIN to remove- Also, shag carpets were apparently a thing back in the day so get ready to rip those bad boys up and replace them or refinish the hardwood if possibleThere is much more of course but those are some that I definitely noticed right away and are what I plan on tackling, priority wiseAny questions let me know!

As for the tenant, if you are supplying window units temporarily, they have no leg to stand on.

They have windows, doors, siding, shingles, tile, hardware, tools etc at very low wholesale prices.  

Previous owner had wall units for heat and window units for AC. 

The easiest way that jumps to mind is if you have a basement, you might be able to put in an egress window for a couple thousand bucks.

@Caleb Bryant, yup - new roofs, windows, fencing.

Hard money cost me 2 points and 12%, but had limited underwriting, they requested very little in terms of paperwork and the property could be very rugged (we had termites, rats nests, loose wires, holes in sheetrock, broken windows.)2.