For example, I know a lady in my local market that is very successful in the land business and has developed a niche that cashflows very nicely, without a lot of stress, as she puts it though I can't imagine how that is possible. 

Not sure if this is helpful, but I am local to Columbia, SC and have interviewed a few local companies which all seemed horrendous.

I saw two recommendations to attend the local REIA.

Research comps in the Milwaukee area or connect with a local appraiser to estimate your property’s potential value.Depending on the rental income, you might explore DSCR loans for your refinance, as they rely on property performance more than personal income.

Does that mean the actual manager or a local contact.

@Kieran Collings - I'm an investor, flipper, and own and run a local property management company.  

Have you done any research on purchasing property locally?

I write "competition" in quotes because I collaborate with my local "competition" instead of competing with them - common among MTR operators.

I have a close associate with a large project there and the local banks have turned off the spick-et on funding his developments and these are very large multi thousand acre deals.

Reward in RE prices for risk of course.As for horizontal I get mine from local community banks ..