I would look into assets that are non-correlated to the stock market or real estate, as well as tax advantaged assets to help shelter your income. 

With experience in construction and sales, you'll definitely be able to use those skills to your advantage when doing value-add deals.The better the deal is, the easier it will be to do the BRRRR method and you can find some of the best deals off-market, so it's important to build a solid network and create deal flow so you can see as many opportunities as possible. 

If you decide to sell and find an investment property with a greater cash flow potential.A 1031 exchange would allow you to indefinitely all of the tax and use it to your advantage to reinvest into larger nicer property/properties.

On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

To 1031 it doesnt make a lot of sense IMO since $100k of equity going into a new property with 7-8% interest rates will force us to look into markets outside of Oregon, require a Property Mgr at 7-10% and we're almost back at square one unless its a MF with great cashflow.The main considerations for liquidating the brokerage account are: capital gains + OR state income taxes will be brutal, I like the idea of tax advantaged real estate gains AND growing real wealth and assets, not paper wealth.

Gifting her cash simplifies ownership but forfeits these tax advantages and requires filing a gift tax return for amounts over $19,000 (2025 annual gift exclusion).

This can provide more lucrative opportunities by allowing you to take advantage of lower closing and holding costs while keeping much or all of your money out of the deal.Every investor starts somewhere.

Another downside is you loose on the advantages, of the Federal Tax Code, by not closing in the name of a LLC (you can elect to have a LLC taxed, as a S Corporation which is a whole other conversation).If you want to close in the name of a LLC, Mortgage Lenders will offer you Commercial Loan Terms (25-30% down, a 15-25 year amortization, and a ballon due in 5-7 years).

There are also some tax advantages to self-managing. 

That way, we won't run into any of these problems in the future.Also, a property manager would've been able to sniff out a tenant looking to take advantage while touring them.