I think the best emotional support for you will come from a change of thinking. 

The upshot may be that you go with a classic 70 to 80% LTV commercial loan, but it seems you might have a cash position to support that just from the stocks.

I do loading calc all the time for support beams, foundations, footings, framing, etc.

They have a strong W2 income to support taking on debt. 

We listen to podcasts, watch webinars on here and their you tube channel and bought a few of their books from Amazon that you can also get here at the "Bookstore" tab at the top. 

The ability to make a positive impact in the infrastructure of local neighborhoods and economies continues to win investors.FAVORABLE LEVERAGE/DEBTMultifamily benefits from the most favorable financing treatment of all real estate asset classes, oftentimes receiving the most competitive interest rates and longest amortization periods.This favorable environment is led by agency lenders, which were originally created to support housing stock.

I found some podcast channels to listen to, bought some books and added local counsel meetings to my calendar).My first thought about vacation rentals is place like Hawaii.

Being on a team is personal preference, but I prefer it because I like the camaraderie, support, and accountability of a team. eXp Realty also allows you to make your full commission on a couple of your own deals per year (minus a few minor fees for the transaction), which I find very helpful in general and as a real estate investor. 

As others have mentioned, you must qualify to support the mortgage payment for a second home plus your primary residence expense.

Now we are installing new beams to support this 100+ year old home.