Hey David, I was in your same situation a few years ago, here is my advice.
- How does this strategy sound to you experts?
I think this is a great strategy especially if you can partner with your parents. One thing to consider is how big of a 3-4 unit you will need. If your parents want a 4 bed two bath and you want a 3 bed 2 bath plus one or two rentals make sure you budget correctly. Real estate is like anything else, you can talk about it and read about it all day but you really don't truly understand it until you do it. I see a lot of people doing all these crazy calculations on 3 and 4 flat deals (When I started i did it too, ha). If you can't do a your first 3 or 4 flat deal on the back of a napkin, it is probably not the deal for you.
- Will this strategy impact my long home buying abilities 2-3 years from now when I am looking for my long term residence, and if so how?
If the deal is in your parents name it will not hurt you at all in the future. Just make sure it is completely in their name and it does not show up on your credit report. To the bank you basically just live in your parents home.
- With the property I intend to purchase 2-3 years from now I would hope to get a 15 or 30 yr conventional loan, but what should I consider for the investment property (hoping to put down as little as possible).
I would look at the new 5% down program from Fanie Mae. FHA is 3.5% down but anything over a 2 unit requires a cash flow test, with rates where they are I hardly ever see anything in Chicago that would work. The max for a 4 unit right now is 1,396,800. With rates where they are you will likely have a hard time cash flowing unless it is a big value add deal. I got close to using the 5% down program about a month ago on a Bucktown 3 flat. There was a job change at the last second and I had to go a different route, but it is a great program.
Hope this helps. Let me know if I can answer anything else for you.