You need a reserve to handle unexpected costs, particularly during the first 1-2 years of ownership and learning how to manage the property. 

Managed and renovated entire triplex in a newly revitalized area.

Wherever you invest you'll want to focus on building your Core4 team of an investor-friendly real estate agent, lender, contractor, and property manager. 

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?

Be sure to factor in contingencies for unexpected costs during the rehab process and maintain a realistic cash reserve for property management and maintenance.

These are always hard issues for managers. 

Let's talk,DanIve actually been looking into buying a condo myself as an investment, I have a few rules, needs to be with both good hoa management & relatively cheap fee (bellow $600 a month) needs to be in area where I’m not competing against other new construction apartments, needs to be an area where even townhomes are so expensive you are not competing, I.e. upper nw, nova, Bethesda etc. needs to be 1990’s or newer in most cases.

I have used TurboTax and Taxcut, so I am looking for an accounting/property management software for Mac.Thanks in advance.

However, I’m actively managing my investment, taking on risk, and improving the property, which has significantly increased its value.

I'm looking for a spreadsheet or tool to use an example to log and track hours spent on real estate Managment.