Remember also, you can never go back and contribute to these accounts if you pass on the opportunity now.In terms of the condo, I am not a fan either, but if you already own it I would run the numbers and see if it makes sense as an investment.

You haven't given a lot of detail here- but, I am a huge fan of HELOCs.

In houses with exterior slope towards house, I like a passive approach; exterior French drains (I'm not a fan of sump pumps--they can fail). 

Also I will disclose that I do not know your area at all so consider anything I said just me throwing words on the screen that one little piece of data could make completely invalid any longer.Personally I am not a fan of renting out places with an HOA.

I am a huge fan of buy and hold investing, specifically in apartments.

I'm not a huge fan of window wrapping in rentals, but with the lead paint problems we have down here in Pittsburgh in older residential housing from the 20's and 30's, soffit and fascia wraps are a must, especially on brick-veneered buildings, which really makes the peeling paint on the other facade elements stand out.

That being said, mixing business with family and friends, not something I am a big fan of. 

He says, that over the last 10 years, he replaced ceiling fans, and doors (all UN-authorized and news to me) so that should be considered rent money.

I'm a huge Pittsburgh sports fan and a fan of sports and competition in general.

Not a big fan of carpet in rentals, it rarely survives one tenant.