After about a year of slowly renovating (doing any work we could do ourselves) we noticed property value in the area was rising. 100k+, 140k+ homes were now on the market, and these homes didn't have what we do: a corner lot, garage and a safe family friendly park across the street.

I host a pitch free monthly meetup in Orland Park that has some flippers, buy and hold, BRRRR, contractors etc.

@Michael Parris there is a good meetup group going on tonight is Asbury Park at Cibo e Vino, I think it is called.

The home was originally built with four units but the city said there wasn't enough parking (so each 5bd unit basically has it's own connected 1bd mother-in-law apartment with kitchen and everything).Here are a list of my concerns: 1) Deferred maintenance  (a lot of vinyl flooring in bad condition, original roof may need to be replaced in the next 5 years, etc...).  2) Fewer units make vacancies, or a bad tenant causing damage very costly. 3) I don't have the cash for the down - I either need to find a partner or sell or refinance an existing property.To address some of these concerns: 1) I have a handyman I've used for years who could hammer these things out on a schedule that I could afford.  2) I've never had an issue keeping my unit occupied (I've even had the same tenants in one unit for over 6 years).  3) I've never partnered, but I'm willing to do so now if I can find the right person.Please share your advice!  

What is the parking situation?

General rent- ability is also important in terms of unit layout, parking, laundry, accessibility, etc...best of luck

Is this the one with underground parking?

However, just like anywhere you are in the country, there are going to be some areas, that are simply not a favorable space (East Cleveland, Cleveland Proper (except: Tremont, Ohio City, University Circle, Gordon Square, Duck Island, Battery Park, Detroit Shoreway and a few more notable spaces)) moving on, the remaining eastern communities will give you settings featuring lower-middle-upper middle class, as well as premium upper class communities, but they do not seem to be on your radar anyway.

All of a sudden a car pulls up to the front of the house (parks on the street facing the wrong way)  jumps out of his car, runs up the lawn and flings the front door open and flies into the house.  

The number of units you can put on a property will depend on the density allowed in the area, set backs required, availability of utilities, sewer, parking requirements, roads required, etc.