Can you guys please chime in? My wife is concerned that my goal of purchasing one home per year over the next few years will prevent us from buying our own home (currently renters) in a couple of years when we move back home. My thought is that we have the VA loan available so we can purchase with zero down when we do move home and that positive cash flowing assets will not look bad to a loan officer. She is of course concerned that all of our money will be gone (it won't but we have the VA zero down loan anyways) and even if we still have savings, no one will want to give us a loan because of our LTV/DTI.

I'm trying to weigh and compare having say 3 performing investment properties in two years and then applying for a VA loan vs buying our primary residence with 20% down then trying to invest with a HELOC. I think I know where I stand but want to get her as much information as possible.

Another obstacle I won't go too far in to is that my mother-in-law is trying to convince us to buy a rental back home in Hawaii that will negative cashflow. She is a broker (not an investor) and just wants her daughter to have some sort of obligation to come home. That's all about that :)

Any advice is appreciated. Mahalo!