------------------------------------------------------------------------Here's our current guess: "The builder's plans and the build may not line up perfectly, so the buyer could sue for breach of contract or a similar claim."

Make sure there is a good number of comps with that similar layout so you know you can sell the property. 

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?

Similarly if you currently allow smoking you cannot change the least to prohibit smoking. 

My Canadian partners and I bought a Class B 144 unit in Houston, Texas for 77k/door and we’re actively looking for another similar deal.

Anyone been in a similar situation?

Investing in the right neighborhoods can increase your odds of success.Also if you look at the appreciation rate in Cleveland and Dayton over the past 10 years its actually quite similar to the cities of Columbus.But I do see your point of being careful in "declining population cities".

Your tenants can only continue paying similar rents if they remain employed at similar wages.

Would love to hear from others in similar situations or with more experience.

@Patrick Osterling similarly I come from a sales background as well.