- central location - Sunny days- No natural disasters or man-made for that matter- great public transportation - revitalization of Downtown and a burgeoning Arts District- terrific Airport- excellent health care options- moreIts a sellers market everywhere.

If this is the case then you can deduct all transportation expenses (i.e., costs of getting to and from the destination).  

The house is about 1400 sqft and is close to public transportation.

@Kusum Chanrai One way to speculate on heavy upside is turning to areas which are soon to be better served by public transportation, for example Chinatown which will soon see the extension of the Muni Metro T Third line through the financial district.

It's like buying a Ferrari when all you need is a bicycle to transport yourself one mile to work.

Haven't spent much time in the neighborhood, but there is low crime compared to the rest of Chicago and public transportation nearby. 

For public transport, ITP east (Belvedere-ish and out, and west are your best bets, or the south (College Park, East Point, Ft.

You could also focus on the great financial advantages of renting/down-sizing (travel more, no more yard to care for/repairs, buy an RV, visit family more)Host a senior-focused event at your facility (maybe show an uncut version of Woodstock haha) or live music, a Social Security expert speaker or Doctor to address health issues, a fund-raiser, art show, etc. and hand out flyers with a special "one month free" coupon attached Have exercise classes for seniorsWeekly bingo nightsPromote your events for free on community calendars, newspapers, seniors sections of papersPrint door hangers and get some kids to hang the door hangers at trailer parks, older communitiesEncourage your current tenants to invite friendsRent a 15-passenger bus ($50) and offer free transportation to key eventsSponsor events at senior centers in the areaCo-Sponsor service club (Rotary, Kiwanis, etc who have many senior members) eventsPut up banners and balloons when you have eventsI hope at least a few of those ideas might spark some interest.

looking at a 4 unit townhouse. up and coming(hipster) location. close to transportation.

@Mike AbramovMy take on this is pretty straightforward and why we self-manage our local properties: property managers work in an almost completely unregulated business.