I'm really looking for something with multiple units, i.e. dueplex, quadplex, etc but it looks like the supply is mostly older single family homes. 

Quality (A is remodeled like new, B is a clean older house with some updates, C is a dated house but not bad, D is dated and needs work, E isn’t even worth caring about… D actually isn’t even worth noting)3.

I'm looking for ideas from more seasoned investors/builders/developers to figure out the best use for this property. 

I've been getting some resistance (naturally) from some family members, so it's a little stressful not having their full support. they think it's a money pit since it's an older house (1920) and will constantly need repairs causing me to lose all my money, and dont like that its out of state (1 hour from where we live, not terrible).

Only suggestion I would give you is to check with local banks about refinance seasoning.

I am just a lucky guy and things could have gone the other way if I was 5 years older and had invested in 2006 or 2007.

I am communicating with a gentleman from Canada who would like to invest in us, 0% down and only 5%-7% interest, depending on the deal.

Also, on these kinds of loans, will lenders require that I season the rental for a period of time before I can take out the loan?

Surely, I am not heading up as often because of a newborn, but will try to do so once she is older. 

Include capital expenses and maintenance, which will be higher than average for an older house and lower than average for a brand new house.