I actually consult and help other owners get property bookings as well3.

And on the same note, you need to cognizant, just like residential, if your tenants can actually afford those increases.  

Ways to finance these projects are using hard money, you can also use conventional loans where you can finance as owner occupied but they cannot be properties that are not livable they need to be properties were you can actually live in.

If not, and I have to actually get a real estate license first, how do I find a sponsoring broker specifically interested in this arrangement?

If you feel the need to WIN at the buyer’s expense without taking actual cash out of their hands agree with the option period being extended to 4 years.

The first consideration, in my case, was that I could afford the first loan since the property I took the loan on for the downpayment was rented and would still cashflow even after I took that loan.The other consideration I made was ensuring that the new property I was acquiring would also at least break even with the monthly payment for its loan.The third consideration was that I had enough money saved not for the downpayment but for at least five months of payments on both properties in case I couldn't pay the loan in case of an emergency (you never know if the new property will rent immediately or when you will have unexpected costs associated with either property, etc.)All three considerations were very important to me, but for my peace of mind, number three was the deciding factor.With this strategy, it could seem that I am making less money since I am racking up new debt on the rental I owned to begin with, but the way I see it, the appreciation I will get in a few years and the actual cashflow that I am still getting were completely worth it.

You have probably missed the appeals Window for this year.Your taxes could actually more than double since you probably have a baseline home exemption limit.Your taxes are the combination of your valuation and the tax levy rate.  

Now I have come to conclusion that I actually would love to invest, and become one of those landlords.

Make sure the current assessed value is w/in about 25% of actual market value or you will have to underwrite in a decent property tax bump w/in 1-3 yrs.   

We are actually up 14% bookings YoY 2023-24 so I am still optimistic about the market overall, but it likely will never be like 20-22 ever again.