My goal is to buy and hold single and multi-family units as a form of "retirement".  

My question is, Can I deduct any of the repairs and reno costs as part of our rental hustle (Not forming an LLC yet) even though the house is technically Owner Occupied while the repairs are happening?

@Alyscha Johnson,You may want to see about getting over that.REI is a people business from both ends: people for whom you provide clean, safe, affordable housing and people with whom you associate to meet your common REI business goals.It's not easy for me, so I can identify with you a bit.

A quick web search looks like Montana is pretty lenient on disclosure forms, but you should check with your local real estate experts to be sure.If a buyer learns of it I would certainly expect them to want a discount or to shy away from the property.

Hey Nicholas, Aaron from visionary plumbing did a good job for me.

A cabin 20 mins from Killington with summer appeal (not far from White River Junction) seems like the perfect entry point for me and quick recovery of upfront costs after a few successful winters and break-even summers. 

Since you and your brother are entitled to 1/3 of the profits on said property, this is a complete gift and your father needs to file a gift tax return, Form 709.

One idea would be for me to contribute 20% of the funds plus everything mentioned prior while he provides 80% but we split the profits 50/50 what are your thoughts and/or experiences?  

And thus I have to find other financial mean, outside of my career, to find the means to make sure he has what he needs.It amazes me how many different paths can be set upon with REI, the question is always 'which is the right path for me?'. 

There are forms of "illegal flipping" which involve selling a property on CD to someone with a large down payment and a poor ability to pay.