Hi Kurt,
Thanks for your questions, it allows us to explore our own thinking.
Our other homes were not "flipped" intentionally they were homes we lived in for years. We never thought of them as "flips" until now. However, we did buy them for much less or distressed and worked on them. We didn't just ride the appreciation rate up on them. Home we are in now was bought with cash out of forclosure for 68,000. Home before that was a 57 acre farm in KY, we brought the farm and home back (very distressed) and then worked the farm for 5 years, we bought that with 50% down (cash) financed the rest through a small bank in town.
Our credit score reflects years of no debt. We were completely debt free for close to 10 years (Dave Ramsey). We liked the freedom of no debt but it isn't good for a credit score. So for the past year we have been building credit again. Takes time... no credit seems to be a more difficult hurdle than bad credit. We still don't have a lot of debt, we keep it low as we still like our freedom.
All that being said, we are sitting on money in this house which could be working for us now. We could wait and save, but we aren't afraid of the "risk" we are more about the opportunity. With our skill sets our time and money would be better used in an area with a much better economy (not here in the very north country). We have planned for a 50% vacancy in our vacation rental here, which seems to be very conservative, as we live within 30 mins of major ski areas and in the summer these mountains are filled with vacationers from NY, MA, CT and RI. Lots of rivers and lakes up here, great place to vacation. Even with a 50% vacancy rate this home will support itself and put money in our pockets (4 bed, 3 bath completely renovated antique cape sitting at the end of a dead end road surrounded by pastures). Our daughter will be the property manager as she only lives 20 mins away. We could take the vacation rental money and just use it to pay back any equity we have pulled out. As long as we are as successful in FL with our homes, we should not need any income from this home. The worst case scenario is we move back here and keep doing what we are doing. We could pay the mortgage on this home without a problem. Or we simply do in FL what we are doing here, as we get our REI off the ground.
Personal note- We drive upwards of 4-6 hours a day to do what we do here, because we work renovating and construction for others. Our area does not have a booming economy it is very seasonal and mostly vacation area. All the money in this state is in the southern portion of the state and those are the folks calling us to do their work. Our time is being wasted in drive time and it means really long days with no time with the family. We could be working for ourselves, and doing much better (we aren't doing badly our company made 250,000 last year) but we have to spend twice as much time making that money as we would in a better area. Tired of long winters that make our job and work harder. And tired of working for others when we could be doing better working for ourselves. So that is the personal side of our thought process.
We aren't afraid of the risk, we don't want to be foolish however, so we very much welcome anyone that would like to analyze our thought process and give us feedback.