@Anthony White I think a portfolio loan with a local bank would probably be a good idea.

The Chicago laws are not only tenant-friendly, but black and white which doesn't allow for a judge to use common sense.

Typically they will sit down with you and do a tax projection as often as you need, monthly/quarterly annually, etc.   

@Tim LaBelle You are correct, we are not quite as agressive as most of the costal cities, but like Rebecca said the North Shore is one of the most desirable neighborhoods in Milwaukee, properties in good condition go fairly fast, typically in days and we have seen some solid appreciation in the last years.

That's definitely not what the the typical Marine is concerned about.

On your primary residence you should be able to get a HELOC for up to 95% of the current value of your home, subject to DTI restrictions of course (typically 50%). 

.% down of the purchase price and the rehab costsCan be used for primary residence with 1-4 units (could also be looked at as a disadvantage)  When using 2-4 unit property, projected income from other units can be used to qualify 6 months' worth of mortgage payments can be rolled into the renovation budget if the house is deemed uninhabitable by the HUD consultantCredit scores can go down to 600s (lender dependent) DTI can go to as high as automated underwriting system allows (typically 56.9%)Allows you to buy a property in any conditionCan use it to fix minor repairs all the way up to basically a full tear-downFHA 203k Disadvantages: Interest rates tend to be about .25-.5 higher than regular FHA loan Additional costs include HUD consultant fee, inspections, title updates, and supplemental origination fee (Cost of doing business, but this is built this into your numbers, so it's no big deal)Must use a licensed General Contractor for a full 203k or up to 3 specialized contractors on the limited 203k Must hold onto the property for 1 year and live in it. 

@Matthew Paul what is a typical rental costing you all in after repairs?

They'll typically be more flexible and you'll pay less for borrowing the money from them.

The Landlord is typically expected to maintain the property in the condition it was in when you occupied.