I am extremely new to this world and trying to figure out how to analyze potential properties. 

In some cases people decide not to do a cash out because the rate on the first is extremely low but even in those cases cash may be the wiser choice.Here are some issues with a HELOC - They are a liability, open end mortgage (basically a credit card) - They carry a ARM or Fixed Term rate set for 3/5/7 years with generally a higher rate then what you could get on a 30 Year fixed currently (Especially for the lower loan amount under $80K) Yes - they can hurt your credit because again its a open end credit card so when the balance gets above 40% of the credit limit it will have an effect of the credit score.

I lack the confidence to pull the trigger since the homes are so expensive.

We just want to get our ducks in a row so we can pull the trigger when the time is right.

If it can mitigate your cost of living over the next few years, will cash flow when you move out, and there's not extreme volatility of the industry there (just a steady slow down) - I think it is worth purchasing. 2-4 unit owner occupied's are the best cash on cash in the game and a great starter education into real estate investing.

I'm not sure how you don't see the logic in this Bruce, it's as though you want to jump to the most extreme option first. 

If so, that would trigger depreciation recapture on the hot tub, which seems like it would essentially wipe out any benefit I had from taking accelerated depreciation, right?

I have been trying to get some JV wholesale deals going as I have a list of cash buyers, but everyone I am trying to JV with either flakes out on me last minute or are extremely inexperienced so their numbers look terrible.

When you pull the trigger on your second VA Loan, make sure you understand your remaining eligibility.

Don’t just go with one person’s recommendation, it’s an extremely personal choice and where you end up should be where you feel the most comfortable and that you will have the best chance of success there.