I have them tell me how long a project will take to complete, and then I add buffer days or maybe up to 2 weeks, depending on how long / complex of a project it is and potentially accounting for weather if it is outside work.

would get estimates and see how long to recover the money and your long term plan for the property

I'm passionate about creating secure, long-term housing solutions that balance tenant stability with strong returns.

I think if the end result is affordable housing people need to be invested in their own housing otherwise a good percentage of the beneficiaries of your program won't care.  

Cleveland is a great market if you know how to navigate it and have a good property manager.

I'm interested in flipping, and short-term rentals at the moment to build good cash flow, then pivot into more of a buy-and-hold/appreciation play 10-15 years from now.

I was wondering what are some good areas to look into for investing.

That path does not end up in a good place. 

Good you are researching this topic - I also love subject tos and have written a book on the topic.  2. 

MTRs fall into the standard long term rental( 30 day +) category and will follow those regulations set for Long term rentals.