My goals with the money will be to retire early, travel (I am a Flight Attendant), pay off my parents mortgage, give back to those in need, save money, and be able to do the things I want to do without the burden of constantly worrying about money. 

Let's do a quick (I hope) and dirty look at it:1 - 100k SFH bought with a standard NOO Mortgage at 5% which rents for $1k, and lets assume; that unicorns exist and fart rainbows, you have 100% Lease Up, and $0 for repairs for the first, lets say, 5 years on all of your properties, and that we buy everything on the first day of the year.Year 1: You Spend 30k to purchase house, you owe 70k your payments are: 376 a month giving you a free cash flow of 1000 - 376 = $627!

you're just swapping a rental payment for a mortgage payment to build equity.yes, you can try to spin up off market leads; it takes a lot of work. 

You have an affordable place to live, about half your mortgage payment is paid by the renter, you get to dip your toes in the investor/landlord waters, and you are in a market that should continue to appreciate in value.I recommend reading and educating yourself while saving up for the next investment.

It would help pay part of the mortgage but in the end, decided not to do it.

Ok, so to be clear @Steve Ford, you are looking to get a 2nd mortgage on a 2nd home you currently own?

I'm also from CA but down on the Central Coast, although I spent a good 10+ years in SF proper, Walnut Creek, etc.I primarily invest in Detroit and have been since 2019 (12-doors there now).

There isn’t much to be made in terms of commission so many loan officers don’t want to mess with them, and any loan is going to have fees associated with it of course…how high the lender’s fees are and how low the loan amount is will factor into whether or not that loan is compliant and can pass as a qualified mortgage. 

Train them the proper time to reach you 9-5pm and in case of emergency Dial 911 before calling you.

I am currently in contract on Molokai but can by no means afford a $3500/mth mortgage payment without STR opportunities.