That said, I am sure there are other investors that have a better system for the lower priced properties and areas, and they are doing well - just not my cup of tea.Also, remember, there is a reason those cashflowing properties are cashflowing that much and it is usually due to lower demand (i.e. desire).

My intuition strongly indicates that the most desireable core areas not only appreciate the fastest, but tend to go down less during recessions.

I have no desire to act as a free bank for tenants but I get the sense that I can't just say "no" to refunding prepaid rent.   

I know that this is very close to covering the mortgage, taxes and insurance but SFH's down here are really expensive unless we go to a not so nice neighborhood which will in turn convert to not well desired tenants.Thanks for the tip.

To give some context, we are in a very desireable neighborhood in Chicago, close to transit, restuarants etc. 

@Alex Chin always has good advice, and I can't add much to this thread except my usual rant about data-driven processes... ie making your own databases from assessor data and tagging/marketing to desirable parcels.

I have to agree agree that the rental market is less than desirable in our area right now and you may have a hard time breaking even.

But even this is subjective, since nicely remodeled will have a premium to dated, but an unusable, large home will sell at a discount when viewed as per sq ft value.For a comparable finish quality, on equally desirable street in same neighborhood, we have sold properties almost exactly at the same per sq ft price as smaller properties, but they were equally usable as their smaller counterparts, i.e. 2,900 sq ft 4 bed 3.5 bath versus a 1,900 sq ft renovated house 3 bed 2.5 bath

For example, if you are looking to connect with other members near you, want to learn from people in a specific area you’d like to invest in, or have a desire to find people interested in certain topics, you could use the search feature here: https://www.biggerpockets.com/search/users

Some investors choose to deal with issues to achieve more desirable yields and higher equity multiples.