Hey @Account Closed, great and articulate post.
I would say a few things: 1. Yeah, it seems like the market is high. As you mention Riverwest or Bay View, I'm thinking that they don't cash flow all that well, especially if you factor in a PM (with placement costs) and longer term capital expenses. Furthermore, the rents aren't that high, maybe a little more so in Bay View, but not relative to the purchase prices and the tax bills. I see that stuff in Bay View moving so high I don't even look at it anymore, and the beat up ones that hit the MLS still sell so high that there's no equity there for the investor. Those you need to buy off market - tough to find. Stuff on the south side, even with lower rents, can cash flow a lot better than these Bish class neighborhoods, if handled well.
2. I think with your current resources you can pull off just about anything you want, you have a lot of power there ;) You could leverage your resources in any number of ways. But that might still be confusing, so I would say you need to just dial in the following questions to start:
1. Do you want cash flow or debt paydown? Cash flow can replace your income, that debt pay down can replace your retirement.
2. Will you work in Cish class neighborhoods? If so, you could probably get to that $2,500 a lot sooner than 5 years. (FYI, a property manager friend of mine likes to stress how NON-PASSIVE this actually is, lol. Then again, he's on the front lines).
3. Do you want to finance your purchases or network with off market folks and try to buy them at a discount?
I guess that's it for now. Best of luck, and come to our Brew City Meetup on March 14th, should be tagged somewhere around here on BP as a local meetup. Great place to start making some connections.
Oh, as for local banks, I don't have too many mortgages at the moment (they won't give me any), but Landmark, Waterstone, Equitable, and Waukesha state bank are all local and more or less investor friendly. If you need an interesting product one or the other might have it. (E.g. Waukesha State lets you put down 15% on single family investment purchases, Summit Credit Union lets you cash out into an LLC w/ no seasoning period, etc.)
Best,
JTM