The terms on the HELOC, if you can find one, will most likely be worse than a cash out refinance term sheet I am planning to cash-out refi as much as possible.

Are you cash flowing the property?

I have some cash and want to make it go as far as possible.I appreciate the advice.

I want to get him to understand if our monthly payment is too high, we don't have the extra cash lying around to fix up the other unit and get it to market rents.

Team up with another investor or a person who knows a lot about real estate to help with the money needed upfront or extra cash.

I need help deciding if I should keep my primary residence and rent it out or sell it and then move into a new one, I have already done a cash out refi of 60k if we rent it we would get 150-250/ month profit not counting cap ex and if we sold we could get 5k-20k property is worth 250-280 ARV , the property has brand new roof hvac and hardwood floors with in the last year or two we will also be using va loan to buy. ps my wife wants to sell and I want to rent it out 

Cash Flow: Decide whether you're aiming for long-term appreciation (ROI) or immediate cash flow.

I only invest in Sacramento, cash on cash is decent.

Vacation homes take some planning, I personally think shooting for break even profit/loss with a vacation home is a good tax strategy but if it is a cash cow I would gladly just pay the tax as you still come out significantly ahead and if you have one I probably wouldn't bother with a cost seg study unless you are getting extremely high rents.

I would be using a mix of cash and pulling equity from my home so ideally I can maximize my investment dollars as much as possible.