If its within a reasonable window, it'll probably appraise for the higher contract amount unless there are very strong comps.Get a contract drawn up and work with an attorney (not sure if you all use them out there, here in Illinois we have to).

On the residential side, you can have up to 10 loans per spouse (assuming each of you can qualify) and the terms will be much more favorable, but you are approved based on your finances, so if they are strong your experience will not matter  

We have started investing in the midwest but in a market that does not have strong economic growth, but it's steady. 

I can certainly make some suggestions on a Georgia-tested lease, but I've gotta say this first...If you're raising the rent anyway, I would strongly urge you to consider adding in enough margin to have the property professionally managed.Property management is where most buy-and-hold investors lose their shirts!

If you can't reach the owner then try to strong arm the HOA/maintenance man/realtor to do something. 

There many investors in the Milwaukee and waukesha area that are strong believers in the area concerning multi-family buildings, so there are many that're very hopeful for the future of the area. 

Google searches would say that it is strong, but I'm assuming that if varies from street to street. 

I can strongly recommend him. 

@Peter Heldstab All 3 of the markets that you mention are strong cash flow markets, The real key to success in either of them is getting to know the areas and neighborhoods.

If so that seems reasonable but i am not strong on knowing labor prices vs labor and materials.