That said, I see a lot of information about how to invest, but I’m struggling more with when it makes sense to realistically take that first step.

@David V Flores, I'm guessing many people will tell you to get quotes and that may not be a bad idea for something this large but I'll give you another basic method to "estimate":1.

If you don’t already have the caseworker’s direct email and phone, that’s the first step.

A simple step you can do today is pick 2 or 3 neighborhoods you would actually self manage in and pull 10 recent sold rentals and 10 current rentals so you know real rents and real prices, not list price math.

From a tax angle, flipping is treated as active income, so once you start doing consistent deals you will want the right setup, often an S Corp, to avoid paying more tax than you need to.The best first steps are to learn how to analyze deals, build your team (a lender with creative financing options, a real estate agent in the area you're interested in, and maybe a CPA), and understand your numbers so your first flip is profitable after taxes.I just sent you a DM with a resource that might be helpful for you in this situation, so feel free to check it out.

It's wonderful that you're taking steps to secure your financial future.Research the Market: Familiarize yourself with the real estate landscape in Portland and Oregon City.

Financing is assumed to “work itself out later.”Individually, each step seems reasonable.

I’ve stepped back from active acquisitions largely because the numbers I’m seeing don’t resemble what I’ve historically required, as well as other business and life commitments.That said, I’d like to put this capital to work.Ideally, my investment would have:15%+ annual ROI target cash flow.Ongoing time commitment of 0–10 hours per weekMy current position:Willing to invest upfront time if the ongoing commitment becomes minimalOpen to both long-term wealth building and/or strong cash flow (A blend of both, or strong on one side, and less on the other).Paths I’m Considering:Acquiring additional rentals (if strong returns are still realistic in certain markets or niches)Private lending / hard money lendingPurchasing performing or non-performing notesTax liens / tax deedsFunding flips or partnering with operators Real estate syndications or crowdfunding (though I question whether 15%+ is realistic here)Current obstacles:For buying potential rentals / distressed properties / flips - Locating potential deals. 

Recently stepped into small multifamily ownership in New Hampshire and already deep in the weeds on tenant mix, lease strategy, and local supply dynamics.

I’m going to start using this method.