Not planning for the big cash expenses like roof, windows, siding, decking, exterior painting, lead paint abatement...Every few years I got surprised with a new $5,000-$45,000 improvement.

My thoughts are you could get a place that only needs small improvements, carpet, paint, maybe windows, etc.

References too of course, but those interactions from the phone call to meeting them in person really paints that picture more clearly.  ** Where do you find the hidden red flags?

They'll replace the roofs, paint, etc when needed (IF they managed their funds properly).

Just saying paint often is not good enough, specify a coat of primer and a coat of paint or 2 coats of paint, etc. 

Better to get $30/month more with a fresh paint job and by being a good land-lord, than to $0/month because you didn't get the home.

I think that paint and basic repairs fall under this section BUT If I want to replace some carpet, replace stove and some light fixtures that are broken these do not seem to fall under the "start up" deductions (or am I wrong).

Got one of those inexpensive shower spas as well, painting would have been much cheaper!

Do you have asbestos or lead paint to contend with?  

Home Depot has better quality cabinets for 10/20% more in raw oak, but you have to stain and varnish or paint them.