It all depends on how fast the property is appreciating as well. 

It depends on the rental income, what you plan on putting down (20-25% is typical, 15% or 25% is required for conventional depending on # of units) For your owner occupied deal, you should be able to use a portion of the rental income to qualify and help offset your DTI a bit. 

The refinance step is where you pull out this equity, typically in the form of a cash-out refinance.Here’s how it works:You refinance the property at its new appraised value (after rehab and renting).You take out a new loan based on that increased value, ideally for the full amount or more than what you originally paid for the property.The goal is to pull out enough money to cover the cost of the original purchase and rehab (or even more, depending on the property’s appreciation).This allows you to recover your initial investment, which can then be used to buy your next property.5.

If the client is in CA the community property state laws may help here (not entirely sure) depending on when the property was acquired but it would be a great question for an attorney as Jason mentioned.If they were married and went through a divorce it would be worth looking into how the divorce paperwork stated how that property would be handled.

If I do move in the next few years because of the military, I will decide if I want to sell for the appreciation depending on the market. 

As a few mentioned, depending on your situation you might have to do a DSCR Cashout (vice conventional investment), and with hard money loans often there is a pre-payment penalty.

Another one is when you start to feel a little weight off your shoulders because you don't depend entirely on your boss.

Whether you should take a retirement distribution or not depends on several factors1) How much do you value the freedom/flexibility to ues the money NOW compared to when you are 60 years old.2) What type of return can you get having cash vs investing in an IRA / SDIRA.If you can make a 1% - 2% better annual return in your personal name, it may make sense as the added return will pay for the penalties over a couple of years.I personally cashed out of my retirement account back in 2016 and it was the best decision I made.

Depending on where exactly the property is located they may have some different rules/laws in place.

In this scenario it is very tricky depending on the end buyers finances if you are looking to sell it to an "end buyer" and not an investor. 2.