I got a quote with another house with the same floor plan - just to paint the house would be at least 5K because of special equipment needed.

Quite often the operators in this space will paint the exteriors, add a new sign, improve the leasing space, add dog parks or playgrounds, and then finish with some level of improvement in the interiors of each of the units.

Buzz saw ripping wood at 3 am, or etc...If you dislike the renter interpersonally, well that's another issue.Good Luck!

I always recomend doing a cosmetic rehab (white quartz, white cabinets, bathroom vanity, add in unit laundry, paint) these can be done very affordably and often see a 50%+ increase in rents in the trendier house hack areas like avondale, logan square, albany park, etc.

Put it in the paint, as they say. 

Paint inside and out.

The house needs a new layer of paint (2-3 days job), carpet fixing and some cleaning.Thanks,Vivi

What is he estimating for demolition, for plumbing, for electrical, for painting, for HVAC, for cabinets, for appliances, for flooring, for the roof, etc.?

I ripped up the old carpet, patched gaps in the floor, put down a sound-dampening underlayment, and put new flooring over the top.  

Especially, since I've had a handyman, that loved to paint over the existing, perfectly fine, outlets and switches in my rentals.