Steven, I know a few people who have made great, even close to ridiculous money-99% cash flow, little shot at a lot of appreciation-on the north side of MKE and I know a few seasoned, experienced landlords with fairly deep to deep pockets from other areas, who lost a lot there before finally selling for what they could get quick out of whatever they had and then split back to where they'd made their original money. Now, its what some call a "war zone" but I don't like too much to simply plaster that label all over the place, even if its "high crime" according to even our local paper's "crime map", "murder map" etc because what's interesting is you will find some blocks that live up (or really down) to those terms, dudes hanging out all over, checking me out to see if I'm there to buy "something" from them, etc but then you'll find other blocks that will have many well cared for homes on that block or blocks and as it turns out, many long term owner/occs or long term renters and you just have to go and scope it out to see each area.
I never found a cohesive secret to finding great tenants there, other than "older people" was maybe the closest, BUT it sounds like you have a good or great IT job going, while I applaud your wanting to jump out on your own, be your own boss, etc and say to keep thinking that way, I'd HIGHLY recommend saving up a lot more $$$ reserves first, unless maybe as @William Hochstedler mentioned above, your the 1 in a 1000 superman, but that's hard for anyone to predict for themselves.
Also, one thing I've warned out of towners about buying here when I hear these people raving over our low entry prices and what looks like GREAT cash flow (assuming you get paid your rent) is to figure the city of MKE into your plans BIG TIME and that's double the reason why I'd say to get a much larger reserve, unless you find some new line of credit to tap that's at a LOW % rate, because the city inspectors are usually just fine to work with, BUT the city govt has a big beef with anyone coming here who thinks (and NOT meaning you here!) they can buy in cheap as hell, collect their rents, but do the bare minimum or even be halfway cheap on upkeep and sure as heck tenant safety issues, basically sucking the life and money out of an area that needs some help and contrary to the opinions of many who spend zero time there, is NOT just an orgy of drugs, crime, violence, etc but has a majority of decent people there who likely grew up there, its home to them and even for many who could afford a "better" (ie pricier) area, its still home.
I'd hate to see someone with good intentions like yourself, who is forced to scrimp on something or things due to flat out lack of funds then be labeled a slumlord, since the city has a MASSIVE hammer to whack the heck out of anyone they think of that way, as code just for exterior is basically a like new structure, down to the paint not chipping etc and they can rack up 20, 30+ code violations instantly and then take that "slumlord" to court, get a civil judgement so you can't even just walk away then, it will hurt or ruin chances for any other mortgage, they don't want that happening and I've seen it happen to people who most of the time, did deserve it. $5k won't even cover a cosmetic rehab and the city also hammered the biggest mega banks on REO homes they let slide, forcing them to hire crews I knew to spend $15k, $20k or more JUST ON EXTERIOR WORK, insides still trashed in areas where nothing sells above $50k or $60k, using same tactics. They were going to get the civil judgements and then go after the banks ability to operate in WI eventually, but it of course never got that far and Citi, BOA, etc gladly spent hundreds of thousands, maybe millions on homes that are likely still vacant, just with new paint, fixed porches, windows, etc!
Build that reserve, keep the spirit and then jump in there, its worked well for many!