Also, these floors are 100 yrs old, in some cases, so people are not expecting perfection.  

There is no one perfect solution, just as there are so many opinions.My opinion, for commercial REI, is to first go with the easiest loan you can qualify for.

It is perfectly legal to operate as a duplex because it is the same concept as renting out by rooms.

There is no perfect time to invest and there are better times.

Aloha,You are definitely losing out on otherwise perfectly good prospects with your full interrogation before they even view the property. 

lets say you live in Cleveland or Columbus and a perfectly good house not in the hoody can be what 200k 250k..

It's a perfect place to start your real estate investing journey.Check out BP Podcasts: https://www.biggerpockets.com/podcastGood luck on everything!

I also became a licensed realtor and now assist investors and retail customers in finding their perfect properties. 

I see a lot of deals that make sense if everything goes perfect, but I would not count on everything going perfect.

Its located in an area that I feel would be perfect for Tiny homes, big tourist area, crunchiest part of Colorado Springs, and in a no-man's land part of town that is off the beaten track and with amazing mountain views of Pikes Peak.