You left out a third option. 

You may even want to do it a third or fourth time, depending on your tolerance, ability to manage, PCS, etc.After two fourplexes are under your belt, you can move into a single-family home and the income from the eight rentals should keep paying for themselves and provide cash flow.

I usually wait till the third date.

I wouldn't be in a huge hurry to pay off the student loans yet, but this is coming from someone who only racked up around a third of what you have so the potential impact on how you invest is likely very different. 

Hi John,I would ask for a proposal for both property coverage (direct physical damage to the property - fire, wind, theft...etc.) and liability coverage (bodily injury or property damage to a third party - your slip and falls).

I am wondering if juggling the expenses for a third property, being new with limited resources, is something I should try?

The only solution is to have a slightly-less-well-paid self-employment gig on the side that you can pick up and drop at any time, which is why I have a renovation running at all times, adding to the portfolio.Try to hire third-party handymen, it gets expensive and also very spotty...there are way too many incompetents out there.

I've executed two home purchases using the VA loan (so far), and I'm looking forward to my third later this year.

The best meetup to network with the largest group of investors is the KREIA meeting on the third Thursday of the month.

House #1 is owned by LLC #1, the second house is owned by LLC #2, and the third house is owned by LLC #3.If a tenant slips and falls at house #1 one and sues LLC #1, my properties owned by LLC #2 and LLC #3 are protected from that lawsuit.Aside from the extra liability protection it keeps the financial books extremely organized.For each LLC a new EIN and a separate bank account.