2 years in, Growing Pains! What's the Strategy?

[Luke Tetreault]

My Fiancé and I will be wrapping up our 2nd year of investing part time in the next couple of months. And it seems to be getting less clear on where to head. Maybe you guys can help!

In the past two years we have completed over a dozen flips, We are holding 20 rental units self managed and 2 self managed Air BnBs. Yes we tried everything, and Yes I know now that wasn't the best play haha. We are both 28 years old with zero experience prior to getting involved, she works for the business now and I work Blue Collar in the trades. But as of the last 6 or so months I seem to be losing direction. Where to go from here, how do we truly grow. We haven't found that one thing that has really worked great to catch a ride on the momentum. Flips have done good not great, Air Bnbs are going good not great, and rentals all were brrrr'd perfectly but like most cash flow just enough to pay the bills and cover expenses. I feel a loss of direction and that makes it really hard for me to focus and build.

Do we keep at building a portfolio of small multi family (very abundant in my market, very rare to find anything above a triplex for sale), with plans of selling the portfolio and 1031'ing into larger properties? Do we focus on flipping, (currently we have actually been trying to do this, but we physically can't find enough contractors in our smaller market <100K population to do that much work). Do we branch out of our area and try to do bigger deals now? These are just ideas I have been asking myself.

I think if I could just pinpoint a direction I am confident in, it would make things so much easier to focus and really strive toward. When looking at deals, learning, getting better and thinking smarter as an investor. Right now it feels like we are aimlessly investing, and it makes it hard to see the end goal and even harder to see how to get there.   

I know there's a lot of details missing to actually give an accurate answer. But would love to hear some of your Advice and / or Experience anyone has had as they've gone down this investing journey! Thank You!