Depending on your family's goals, you should consider going straight into multifamily.

I'm not in a position to buy right now, but I am trying to get ahead of the curve and get my feet wet with dealing with contractors. 

Having a great rapport with a great RE agent could potentially give you that quick first step, ahead of any other investors interested in the same properties as you.

@Alex JamaelWorking with investors is a relationship business, so take your time to build these relationships (ideally way ahead before you need the money), show your track record, your credibility, references, and of course offer to help them make some money on the side.

The class rank of the area doesn't matter at all, it just matters how they are cash flowing, what the appreciation prospects are, and how you are staying ahead of repairs and CapEx on each one.

If so, then the treatment for Federal purposes is relatively straight forward.

I realize you are determined to move ahead at this point, but just be careful because renting to relatives often has problems and most any investor will advise against it.

I looked at a chart recently that showed the lake has been below 2005 levels for 15 years straight. 

When you add in the equity paydown you should at least be even on expenses and hopefully ahead on expenses.After both units are rehabbed and the refinance, the value of the property should be substantially higher than purchase price + rehab costs. 

Make sure you are very straight forward with sellers with what you are doing.