If there is ways you can add value through cosmetic work AND negotiate a price to but you in a good position with a fair amount of equity to begin with my opinion would be find another partner to front the remaining amount needed to put the down payment on a HML until property seasoned and then refinance into conventional through bank/credit union.

It's also going to be competitive (high priced) if you are looking in a fairly competitive area such as chicago.

If you plan to buy and hold after you PCS to your next duty station, then it will be up to you to run the numbers before purchasing to ensure that the property will + cash flow once you rent (use the BP calculators or get a sanity check from BP nation to assist).   

We've lived in it for 3 years now, (have a 3 year old) and now I'm questioning my original strategy due to development in the area and because its appreciated fairly substantially while we've lived in it.

I think its fair to say I’ve been terrorized by insurance companies in NH.For the naysayers: Oil tanks replaced 3 years ago.

But it is fairly easy for someone to find out your ties to the LLC with just a little bit of digging.

I'm struggling to find a company that's licensed in Minneapolis that sees the return on giving fair pricing.  

I usually just do what makes sense and seems fair.

Ensure you really analyze the competition and that there is demand for 1/1 units in a rural area.

Fannie also fairly recently allows Airbnb incone to be counted now too