Is this deal too complicated for a newbie?

[Aaron Smith]

The newbie is me and I want to do three things in next twelve months and the first two are related.

I love my neighborhood, but meh about the house. It is halfway paid off and my wife and I would like to move for a myriad of reasons, but we both really like this neighborhood - not the house. I think we should refinance the equity out of this home, rent it out, and purchase the new construction with the funds. This would be our first rental and our goals is not cash flow, rather tax breaks.

Coincidentally, the new construction is in an urban area and we are thinking of building a 1/1 guest house primarily for family that we love, but can't live with. Maybe we will get some short term rental out of it, but it isn't really for that purpose.

Finally I am looking at a relatively new duplex near a military base golf course. For this I would use my self-directed IRA and set up a trust. Again, our goal is to lessen our tax burden and build up assets for retirement.

For those keeping score I want to (a) get equity from primary residence to fund new construction in fill (can I do this?) (b) rent the existing primary residence - home for the last 5 years and (c) use a IRA to fund a duplex right off base built in 2008.

I'm excited and nervous at same time.

Additional details about current home. Updated roof and kitchen in an older neighborhood. I think it needs about $20-30k in upgrades to make it sell, but probably half that for renting. I'm actually thinking about making it an lease option to buy.