So often, I see banks make poor decisions that go against their better interests.

Unemployment is at an all time low.There are more jobs available that people to fill them.The stock market is at an all time high (some say due for a correction)Our Country is combating the trade deficit, which will further strengthen our economy and country.It is still a sellers market and if you buy right and there is a bubble you should be relatively safe.Banks aren't likely to call loans for a rescission if we were to have one.People will always need a place to live.

You might go to a Lawyer/Attorney that regularly working on Partnership and he could probably tell what is the best way to go.I think that various books on Partnerships would help you make the right decision. 

I wanted to make sure I wasn't making a rash decision of considering selling the rental in order to cash in on the profits.

I could HI Kevin,This transition that you're asking about above is extremely important to transition smoothly and plan for because it will ensure your subsequent VA use for additonal purchases.Once the current property is refinanced with a non VA loan this will free up your entitlement for additional use.The max conv limit in Ventura county Ca is 672,750 and the max loan limits for a high balance loan can go up to 95%.So what this means is theoretically you could refinance up to 672,750 loan amount with an appraisal as low as 708,158 dollars or higher before your loan is subject to jumbo/non conventional guidelines (much tougher to qualify for and has lower LTV's).The VA loan has some key features that other loans dont have:- a trade off of no monthly PMI but the upfront PMI is huge, equivalent to 2.15 - 3.30 Points (borderline hard money points).

When this is done, the cash flow off the building will more than cover my housing expenses.One final observation - if you think it is going to take you time to watch the markets before making a decision, consider becoming a lender over the short run (either by investing in hard money loans or re-performing notes).

@George DeberryWelcome to BP, and congratulations on making the decision to invest in your future via real estate.I have written a few blog posts that may help you get started here on BP, and with your investing.

Good luck, and i'm super duper analytical and trying to be paralyzed but also make the proper decision and pull the trigger, luckily I moved from my first home and turned that into a rental. 

I would like to have someone who will eventually buy it, not just a short-term.And I guess my overall question, how do you keep disciplined in making such little decisions?

@Aaron RohnWelcome to BP, and congratulations on making the decision to invest in your future via real estate.I have written a few blog posts that may help you get started here on BP, and with your investing.