Novice here, I've been looking into off-market deals but don't feel comfortable moving forward by myself.

The problem is that each individual is different in terms of how comfortable they feel with leverage.

You can always experiment with what you may be comfortable with to see what works best.Like @Shawn Parsh said, if you have other people looking for the type of property you want to invest in, reward them for their effort.

I think our goal for now is in the $90-100k range to be in a comfortable, wiser decision making spot.Yes, we have an interest rate at 3.375% on our primary residence with about $140-$170k worth of equity (depending on what we could sell it for).

I'm not trying to second-guess your decision, I'm not in your shoes.

If your CPA isn't comfortable or knowledgeable about real estate investing, it may be time to seek out a new CPA.  

That is of course once you felt you've learned what you can, done your due diligence on the property and area, and fell comfortable going in.

Whether you are sacrificing your comfort to house hack, money for a downpayment to cash-flow more, or one of the wealth generators based on the market itself; there is no one-size-fits-all perfect investment.

That gave me a bit more comfort because I wasn't sure if I'd have to fork out for an attorney before I could bid and I was wary of potentially bidding, not winning anything, and then being out of pocket for legal fees.Feel free to PM me if you want more attorney details.

Ask her who helped her move into her unit and suggest you could hire them as clearly she's comfortable with them.