I need to create some kind of significant revenue stream to ensure my wife, kids, and grandchildren are taken care of when I’m gone.

Once you highlight a couple of locations, pay attention to active inventory in the areas by going to listing sites and checking out properties for sale.

During that time I would save and look for a house hack, might be a year or two down the road but you are 21 so who cares. 

He gets to sleep better at night knowing that I am carefully watching and managing OUR investments.

The time spent trying to generate attention to your site would probably be worth just spending the money to air bnb to avoid the headache but that's just my two cents.

Whenever I read investor posts about unit count goals and utilizing section 8 rentals as the vehicle to scale a portfolio it loosely translates to buying real estate without paying attention to the fundamentals in the markets where they invest.

I don't know, but your guy who is self insuring with those numbers is either stupid, nuts, or so filthy rich he doesn't care about taking losses.

So be careful where you buy as some of the coves may not have water during the winter months.  

I did STR in a duplex starting back in 2017 and managed for others in North Conway, Ive since converted to all long term tenants and happy i did so... unless your property has something unique or a "rare" amenity.... like, sleeps 30, I honestly would not waste any energy on it in the north Conway area. so saturated, and so much big money being invested in the hotels, its tough to match amenities vs cost, and I see travelers trending back towards the hotel style accommodations. granted, for the right price, I'd buy anything and figure out what the best use for it is. use airdna.co for decent data on # of Short term rentals in any particular market. can also identify opportunities. the point of my response.... be careful in STR in any area and always have a plan B. you can change a lot of things about a property, but your cant change your basis!

It’s best to handle this situation carefully, keeping the communication open and professional throughout the process.