Now as for your question, what is your main goal?

I would have to travel.. ..to be boots on the ground to network with contractors //bankers...etc..If I overcome the above  hurdles …..

I'll give a little different take....in my experience once you have a legal lease that you're happy with you may never encounter another legal question ever.The tax issues important in terms of frequency because you'll face them every year and taxes are likely your #1 expense beside mortgage interest.The 2 main keys to being successful are that if something breaks, you fix it for the tenant and the tenant has to pay the rent on time. 

I have a lot of learning to do, but my main interest is multi-family dwellings, commercial spaces in the future, possible vacation rentals and/or trailer parks. 

@Adam CraigHI Adam,You like red, a  dark red might work, but  maybe for the trim instead of the door, with sand color for the main part, and an earth color for the doors (front and back) to make them look "inviting".Whatever colors you choose, it's always wise to have the painters try them on a small part of the front so you can see them before you commit to buying several gallons.Sherwin Williams codes:Good Luck!

Here are the main details: - The tenant is currently in a month-to-month lease with the previous owner. - Tenant receives rent help from HUD. - The unit has drywall in the unit that is falling down from the ceiling and may not be a safe place to live. - We want the tenant gone.

My main hesitation is that I live in a strong housing market where prices seem to be forever rising.

(there are some exceptions, so call around your local small banks and credit unions)  Your main option is going to be a cash out refinance, and again, most banks want the property to be in your personal name, not an LLC or trust, to do the loan. 

The property required getting a trust certificate made by the trustee, paying cash for the properties prior to the tax sale and now were are working on obtaining a forced easement to gain access to the main road.

The biggest advantage you will likely have is the ability to use the military's services for notary, that is ironically one of the big hurdles in my opinion doing real estate in the US from Japan.