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

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? 

The only reason I got an LLC was to buy a commercial property because it was a requirement of the lender.

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 believe if people make money and there is sufficient housing supply, housing will become affordable. 

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.

Getting a good painter at a reasonable price requires persistence and comparison shopping.

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).

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!