A turn-key purchase is typically an easier and less risky strategy , but the benefits are less than buying a flip / brrr. 

I'd advise you to pick a service that partners with the Campaign Registry to let you register a phone number in order to comply with TCPA and benefit from optimal deliverability.

I would make sure to connect with an investor friendly accountant to understand the tax benefits you may be able to pursue. 

You might benefit from that.

You must work at least 750 hours per year in a qualified RE business.So most people who have high-earning W-2 jobs outside of real estate won't qualify.But the unique thing about RE pro status is that even if you don’t qualify but your spouse does, you can both file jointly and claim the losses from your RE investments to offset your other active income together.It's an incredibly powerful benefit if you do meet the criteria.

As I see it, consolidating all of our assets under a single holding company offers numerous benefits, including tax advantages, better lending oppurtites, and possibly more liability protection. 

I know a vacancy is tough and it can be hard to find tenants in the winter, but you have to weight the costs and benefits and decide.If it's harder to find renters in the winter, try offering a month-to-month lease just to get through the winter, then move back to a one-year lease in the spring.

-House hacking would be a major benefit.

One of the benefits here is that you can save a bit on closing costs but the PPP (pre-payment penalty) structure may be more aggressive, ultimately inhibiting your ability to sell off if needed - since the loan would need to sustain a minimum debt service.

It will familiarize you with the basic terminology and benefits.