Definiely will offer our time and my wife is a graphic designer, maybe she can design some work for some of them.

There wouldn’t be much activity outside of a little bit of branding and stuff (I do graphic design work so making logos and stuff is fun for me).

This process may be a little costly because it’s a decent undertaking.

Even though you are undertaking a rent-to-own (I really dislike that term, but that's another thread), at this point in time you have a lease and an option contract.   

When vetting a property - even a residential one such as a triplex - nothing should deter you from undertaking a full discounted cash-flow analysis of the property.In this instance, you should first analyse the property using market rents for each unit (regardless of the fact you plan to occupy one unit).  

Likely starting with 2-4 units per risk aversion on the first loan I undertake.

I do graphic design to if you need a photo enhanced, business cards, business identity I'm your girl!!!

There are so many DIY channels on Youtube, with their own off-channel websites with step by step guides. http://www.palatinremodeling.com/top-10-diy-channels-on-youtube/I agree that hiring things out is probably a better use of one's time as an investor than doing it yourself, but I'm of the same mind as you to try to do some of this stuff at first because I'm going to do a more traditional buy and hold pattern where I won't be able to acquire properties very rapidly, so it's not like I'd be missing out on deals by undertaking certain repairs/improvements myself.

He lives on west coast and initially wanted to sell quick, but there is a 86k mortgage left on it, comps in neighborhood are at around 130k.I believe given the circumstances, he would agree to possibly 95-100k to pay off debt and be done, as he has said he has no interest in managing or maintaining the place.My initial challenges and strategies i have been debating..1) To get traditional financing OR asking owner's son to seller-finance, as if i put a deposit down, and he gets to have a check every month and walk away, and I oversee the tenants.2)Owner's son has to get guardianship/POA over the property which is couple grand to complete with an attorney, and takes a few months3)There is a separate duplex next door that is vacant, that i have contacted that owner about that I may be able to contract as well, that could be a nice compliment to this unit.4)Try to negotiate the mortgage/debt down with the bank since the owner(his mom) obviously cannot pay the note any longer, or can negotiate on her own behalf.Any ideas on if this is too big of an undertaking?

Some respond to graphic postcards, some respond to hand-written postcards... etc...