And then when your LLC goes to apply for the loan (one on each prop as you find them) My bank let me know their under writers wanted to see cash in the account that is just sitting there as a cushion.

Should I start selling my rental properties soon since I know it will give me a nice guaranteed cushion in the bank now?

If you are including all expenses in that list, then it is not unreasonable to live off the cash flow *provided* you have a cushion.

I would much rather my first deal in that kind of price range have a really big cushion because I would expect some things to go wrong and want to mitigate the chances of coming out of pocket as much as possible.But california investing definitely seems to be a unique animal where you just have to take your shot.

I have narrowed down my voyage down to a ~5 month backpacking trip through Southeast Asia and I have funds to cover my pilgrimage and transition back into the "real-world" with a decent cushion, but not enough to immediately purchase a home.The question I'm asking here is, if you were in my situation, would you purchase an investment property and get everything situated (finances, tenants, etc) BEFORE you travel, or travel first with the ultimate freedom (time), and focus on investing after the journey?

Should I use the cash flow to help pay down the mortgages or should I use it to build an emergency cushion or are there other options that mght be a better use of the money?

You are probably going to have your property taxes escrowed and it is not uncommon that they collect extra upfront as a cushion.

I just don't have any reserves to serve as a cushion in case a tenant can't be found or if something goes wrong.

They will also need a cushion for any unexpected costs.   

If you want to make some decent money and have a cushion you'll have to buy it for, what, $20K?