Some of these capital structuring decisions won’t age well.

I feel like it's mainly a case by case basis depending on reviewing leases and policies and make a decision based upon the exact circumstances. 

In order to make a decision on keep vs sell it comes down to holding costs, repair costs, total all in costs and projected ARV and rents.

Est of luck with your decision, happy investing!.

We focus on customer service, sales and overall personality when hiring for leasing and assistant manager positions and haven't really made a decision based on PM software experience.

@Derek MorrisonI would speak to your real estate attorney before making a decision on your leasing practices.

Or am I thinking about the problem incorrectly to begin with. 

In Cleveland most tenants have CMHA and the process is a solid 8-12 weeks from the time you submit the packet until the tenant moves in if you don't get held up doing work to pass the inspection, this might also affect your decision.  

As things come up you can make decisions to try to keep the money in line.

A lot of the decision around your best path forward hinges on how you plan to use your cash.