We both have made compromises along the way.I think that’s completely right and one of the reasons you hear the horror stories about these things going sideways (there’s no established timeline for exit), it literally just goes until something breaks. figuring out the ownership structure, and thus the use/access, as well as the exit feels like the two biggest items to get extreme clarity around. 

My 2 biggest issues are getting the occupied units registered as occupied and not Vacant, there is no toggle or selector to do so. 

One of the biggest mistakes an investor can make when deciding to take the plunge and start spending money on Google Ads is targeting the WRONG keywords.It’s true that one way to use keyword targeting is through “broad” keyword types, which are usually less expensive and can capture various keywords you might not have considered in advance.

@Rashim Sharma your biggest challenge will actually be finding a lender.There are two banks that have offices in USA and Detroit that often will lend to Canadians buying in the USA.Can refer you to a Tax Attorney here is the US that has hundreds of Canadian clients with US properties:)

The biggest issue is that eventually those decks will need replacement (I’m keeping them alive as long as I can).

Probably the biggest challenges I see are housekeeping and if you need PM, that could be a challenge.

That is one of my biggest motivations and motor to be able to change my invested money for some freedom. 

Because Chicago is amazing in the sense that it has prices at all levels and tons of old inventory in need of renovation (if you want to renovate).Networking in person was the biggest help for me to get started. 

@Lucas Miller I'm sure he is, but that's giving him a ticket to find his biggest fanboy or fangirl and having me talk with them. :)I'm looking for the unsolicited opinion of someone Lane himself wouldn't call on for their experiences (I'm big on listening and chatting with folks), just to get a sense of what deals they've gotten involved in and how they've gone so far.

Given the Fico on this deal, this is probably the biggest lever you can pull to reduce the total costs.