Tenant had put wall closets, when he removed them there were holes(naturally) so he patches them, so there are big patches(not small) all over the wall in apartment, so need to repaint to look paint smooth.  

Usually everything is smooth until you need to foreclose.

Very smooth process. 

Should I steer clear from these situations or is there ways to make sure its a smooth transition?

Depending on your living arrangements, if you can find an inexpensive duplex where you could live in one unit and rent out the other, you'd be well on your way to smoothing out some tax bumps (and minimizing your living costs).

But be very smooth with your 1st project.

Thus my question is, what would be the best way to go about it, without making any party pay too much and making the transition smooth.  

He is a far family member, so i know he has some trust in me.But i am wondering how to construct the deal so it will benefit us both.He wants to put up about $100,000, to buy a house. we (me and my husband) can put in the cost of the repairs, and project manage the operation. getting the contractor, designing the house and making sure everything is running smooth, wile he is not physically involved.Now, me and my husband would probably need to get a hard money loan in order to pay for the repairs, probably 40-70k depending on the property we perches. 

I was amazed at how smooth everything went on getting the loan.  

It fills in all the low spots of the grain to give a very smooth finish.