Older buildings often have charm and character, but they may also come with maintenance challenges.

The challenge here is making the home ready for their business type AND finding the RIGHT operator. 

Challenges?

Expensive markets can be a challenge, but here are deals to be had, depending on the amount of work you are willing to do.

For some, the potential growth and lack of state income tax might still outweigh the challenges, while for others, the high property taxes are a dealbreaker.

Sometimes I question whether there is some real estate investor challenge I am unaware of where investors actively try to one up one another with new ways to toss their money down the drain. 

The biggest challenge, more than handling maintenance, is managing tenant relationships and understanding the legal responsibilities.

This is particularly important as you acquire more properties.Transferring the Property: If you're thinking about transferring your current rental property into an LLC, be aware of potential challenges that I have personally seenMortgage Implications: Check your mortgage agreement for any clauses related to property transfer.

It just goes to show that challenging yourself and pushing the boundaries pays off big time.

Compared to other parts of the country, in my opinion it's definitely more challenging to find good deals here based on everything you mentioned.