Regardless, I would appreciate any recommendations for commercial real estate brokers, CPAs and lawyers in south central Wisconsin.

What is the condition of the interior?

Most closing companies with a lawyer on staff will do that for you 

No matter what area, condition, or size... first thing you need to do is find a lender or have all your financials lined up to move quick.

My buddy thinks that you have to pay hard money lenders back within the first 3-6 months of the loan (on average). Is this true or are there some hard money lenders that could be used for renting and generating cash f...

I’ve read about HOA’s fees, condition of the HOA and the Board of Directors, slower appreciation than SFH, and difficulty selling the condo.

I'm looking to buy my first rental property, and had a question about liability insurance - I'm buying out of state, and I'm wondering if it'd be best to speak to a lawyer in my hometown about getting a liability insurance policy, or to speak to a lawyer in the city I'm investing in?

As giving them too many thing might create more work and more conditions to clear. 

If it looks like gov't subsidized terms/conditions, it probably is, meaning Fannie and Freddie guidelines will apply.

I'm not a lawyer though,,, but that seems reasonable