Also, I live in Manhattan and don't have a car, making it hard for me to drive for dollars in other boroughs without renting a car (costly but a possible route).

@Mitchell Litam haha yeah I became an east sider by accident when I didn't know what I was doing and now there's no going back, so I guess I'll just have to stick it out over here indefinitely!

@Shane Ward The OP is from the Philly area, so a legitimate alternative option to buying an STR in a market they aren't close to / familiar with would be taking those funds to buy an actual investment property, and using the cashflow to fund vacations indefinitely at whatever destination they choose (especially since they already rotate between 3 different vacation markets due to friends & family).

Although I haven't decided to hold these properties indefinitely, there isn't really a reason I can't just let them pass through my estate and then under current law all the taxable gain goes away and no significant transactions cost are incurred.

I don't think they will continue to be your bill collector indefinitely. 

the 1031 exchange will be fine for you if that property is an investment property,  It will let you defer indefinitely all tax. 

Also given that 75% LTV cap, not sure how many times you could continue to tap the same houses over, so not sure about 'continue indefinitely'.Selling one is definitely an option to explore as well -- although if it is cash flow positive now, possible trade-off of future appreciation if you sell now.All in all, sounds like a good problem to have!

One of my clients is purchasing a mobile home on 2-acres leased for $750/mo and the tenants want to stay indefinitely.

Anybody else buying the dip in car makers/ transportation index because of the new Mexico tariffs? 

Can a tenant sit on a lease renewal indefinitely and sign whenever they see fit?