The best advice ever given to me was to invest in mortgage notes and not the actual real estate...... unless you have the time for value added projects.Know what your end game isKeep an eye on your equity. 

The only catch, is that we wouldn't be house hacking to start, we'd be required to put 20% down on purchase/sale of the property.

My parents live up there, and I'd lean on them to be my eyes/ears.

The land represents ~1% of the purchaseOn the contrary - if you purchase a $2 MM shack in manhattan on a postage stamp lot, the land could represent 99%Lever 2 - % of the property with a shorter useful life.Not all parts of a piece of real estate are depreciated at the same speed.Certain personal property assets have SHORTER lifespans in the eyes of the IRS vs the standard 27.5/39 year livesProperties with tons of this often have:- Over-developed land sites (hardscaping, pools, retaining walls)- Fancy Fixtures- Fancy Furniture (STRs!)

Hurricane Milton Approaching: Hurricane Milton is intensifying and we are all keeping an eye on the news.

If you have a great team, a great strategy, a great eye, you still need the money. 

Then, someone is going to look very closely at that LTV and all eyes are going to slowly turn toward you.  

Local Legislation: Do you keep a close eye on local regulations, especially around zoning and short-term rentals?

I won't bash them too hard, because once in a blue moon there are actual deals you can come across, but having a second filter/eyes on the deal can really be great insurance against buying a dud.

On the day of closing, we drove Anna and her son to finalize the sale, then immediately took them to the airport to catch their flight to Las Vegas.The most rewarding part of this experience came at the airport when Anna hugged us, crying tears of joy.