It is written in our contract that we can make these decisions without the owner's permission for these exact reasons.

This is the reason homes are so much cheaper than cost to build.

Quote from @Havital Miltz: I do not know that if someone is in the hospital you can force them to close, I am not an attorney, but I doubt any court will find in your favor, closings do not always happen exactly on the day that is planned, even if everyone is healthy and well, the wholesaler here is not the reason for the delay so I am not sure what exactly you can sue him/her for, they are also being held up due to the seller not being wellJust give the person some time to get out of the hospital, closing will probably not happen the very next day either, this is really extenuating circumstance. 

The reason to have comparables is if you are representing someone or perhaps purchasing a house for yourself to live in.

I am worried for two reasons: removing the garage will reduce the value of the homes more than the extra unit will add, and the property value will not increase that much with the extra unit(s).

So as a newer person in an area if you want a lot of bids before you close you'll normally end up with the more expensive guys or the ones that don't have work at the moment (usually for a reason).

I recommend checking the areas near University Circle for that reason, but there are some spots not far from there that can be rough, so do your due diligence.

There’s no real reason to jump into another market unless your goals shift and your current market doesn’t fit anymore—or if the market itself stops producing the results you need.Mastering one market and squeezing every opportunity out of it is a much better play than spreading yourself too thin and getting half-baked results in multiple places.

Are there any specific areas that are reasonably priced compared to the cities? 

I'd decide what is reasonable in the market that you want to invest in and create a strategy around that- not what a stranger (who, very likely has never done a deal) says on the internet.Best of luck- happy investing!