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).

If you're dealing with a house that you've unclad and will be reinsulating, and the house doesn't have exterior sheathing or some kind of weather resistant barrier (most houses around here just had siding tacked straight to the stud), you're going to have a huge problem.

Biggest part of the project would be adding a contemporary fence and drought resistant landscape (with a sitting area) to the front yard.

I did the same as others and also put in lease that on outside of property there are to be no open flames or grills of any type within 25 feet of any structure on the property. 

No further need for further vapor diffusion resistance. 

It's easy to get people started because the entry barrier of price is so small, but human nature kicks in and they try to find the path of least resistance and instant gratification. 

I would call it a red flag if they resist giving you everything you request for your DD document list quite quickly, their speed and thoroughness in response to that shows their willingness to sell imho.When you schedule your inspection you want all your professionals there at the same time to go through a single time, contractor, inspector, and any specialists you think you might need like roofer, engineer, etc.Also don’t feel pressured to make your DD and inspection time as limited as is common in SFR, give yourself 2-3 months at least, again, from when they deliver the docs you request.Besides financial DD you want to do physical DD not just on the property via inspections but visiting the area during day and night, weekdays and weekends, to ensure you have a feel for everything that’s happening at different times all the way around the block.

I'm tempted to type it right here but I'll resist.  

And, no, there really isn't a way you can buy it and leave his mortgage in place without a subject-to deal.As long as you are not afraid of being scoffed at, you can tell him, look, I'd normally want to buy this at $100K (I have to resist scoffing at you myself) but I know this is rehabbed and ready to go. 

If there's resistance after my real world talk, they usually filter themselves out when they realize we run a pretty tight ship and stick to our rules.