She advised that since it is an owner occupied loan to be careful as lenders will look for 'patterns' and eventually deny me a loan (but nothing regarding penalty).

I eventually dropped it to $30,000 and had multiple people interested, giving me offers in the low $20s.

I'm just not sure it' wise to flip and hold in the same entity.I will eventually talk with a legal/tax pro so don't worry about giving advice.  

Right now I'm a one man show and I'm not doing it full time, but my goal is to eventually go full time.

Provided you weren't trying to dump under performing properties at the time, you may have experienced some short term heightened turnover if tenants lost jobs in the recession, but I still would think that replacement tenants would have been easily found as it is not like all of sudden millions of people no longer needed housing to stay in, so everyone would eventually land somewhere, right, particularly if you are in an upper income area, where unemployment wasn't nearly as badly affected? 

(It didn't help there was no public internet back then either) I eventually found that, just like all things in life, you have to give up the ghost on feeling like you need to know everything, before taking an action.

I'm happy to have them rent for ten years, but they will buy eventually.

Eventually gold producer's will have to hedge which will be a sell sign and once all the sheep start herding into an investment, Wall Street pulls the rug out form under them.Short term gold will not get much higher than $2200.00 and in five years it will unlikely be anywhere near $5000.00.

Cutting back and sacrificing was necessary to save up money to buy cash...but eventually everyone's cash will inevitably dry up, which ours did.This is when we had to look at financing.  

I live and work in the Bay Area but want to eventually relocate to Oregon, have family near Medford, and feel that I'd be able to travel there fairly easily when necessary.