Advice for nomadic telecommuting IT guy looking to break into RE

[Dana Schreiber]

Hey there, I am new to the BP community, recently been busy going through all the content on this site.  I love Josh and Braondon's podcasts, the forum posts, blogs, etc.  I've read Rich Dad Poor Dad, 4HWW, a few Bigger Pockets books including Rental Property Investing and Managing Rental Properties.  I am at the beginning of my journey here just at the learning phase of things looking to break in on a first deal within the next 3 months.  

I would like to briefly explain where i am in life and seek some general advice from the community members on how to break into my first buy and hold rental.  I am in my early 40s, happily married with 2 kids.  My current job is in IT in the SF bay area.  My job pays me enough to provide a comfortable life for my family but it totally consumes me and has me away from family 60% of the time.  About 5 years ago my family moved back to where we are originally from which is Hawaii.  It's a long story, involved both personal and family commitments.  Through this transition I kept my job in California by converting to a telecommute situation where i work from home half the time and I work from California half the time.  This has been sort of a life hack situation that i negotiated with my manager and i have managed to keep my job by delivering on big projects, keeping my customers happy and just working really hard.  My company supports telecommuting but that doesn't mean managers love it.  Anyone who telecommutes in any company is always under pressure of getting canned if they are out of site for too long, this comes with the territory.  Knowing this I have made it my priority to be visible by staying onsite more (and more) than working remote.  I have effectively been giving up both my time and my location to enable my family to live a comfortable life and this has been killing me slowly.  

I have been edging my way into real estate for quite some time and am both excited and afraid of what the future holds and if I have what it takes to pull things off.  Because of my current work situation I am never in any one physical location for more than 4-6 weeks.  The locations i am in (California Bay Area/Hawaii) are both very expensive locations so finding local RE opportunities that can convert into cashflow positive investments is a challenge.  I know, I know, we are all supposed to be how-can-i-er's and not I-can't-ers on this site.  Mr. Kiyosaki would consider me a chicken little but hey I am not some single guy in my 20's with no one counting on me to keep them fed, clothed and sheltered.  i have effectively allowed myself to get locked into the rat race.  Like so many folks on this site I am looking for ways to slowly dig myself out of this situation. I've been in the matrix for a long time, I am looking for the exit and I'm ready to take the red pill.  

Here are some questions I have as a newbie starting their journey in REI

1 - Would refinancing a primary residence to extract the accumulated equity be a good source for financing the down payment on a buy and hold property intended to be used as a rental? Would a HELOC make more sense? How about taking a loan against a 401K? I am confused which of these is the better/safer option to finance a rental.

2 - For folks interested in buying rental properties outside their primary market, how important is it to travel onsite to see/buy/manage the property?  How often or when should you do this?  I am thinking it would be crazy expensive to travel to remote locations on a regular basis just to keep an eye on properties.  Makes sense to see the property when it is appraised/inspected, before it is purchased and probably spend some time on site during the rehab.  Once the property is rented out i get that finding a trusted and reliable property management company to do the daily stuff and i am fine with paying the 8%-10% for this if the numbers work.