Because of this, I'm exploring what it would look like to begin investing in vacation rental real estate as a way to:1 - Save on taxes by taking depreciation2 - Hold long-term appreciating assets3 - Have properties where we enjoy vacationing that we can stay at when we go to do maintenance (probably 2 areas).What resources would you recommend for someone just starting out who has these specific goals?

If I were to sell, I would look to buy another multi-unit property in a smaller town in the $100-120K range that cash flows $400.

If you're open to exploring international opportunities, I have an exciting real estate project in Dar Bouazza, near Casablanca—an emerging hotspot for residential and vacation properties.

You can manage D grade rentals in rough areas but in general the most success is from those that manage their own rentals in those areas of town. 

He bought a town in Texas (yes, the whole town), but started with land and may have dealth with this issue.

As someone who moved to Waco from Miami just because my wife got a senior position in Magnolia, I've met many families and individuals who have come to Waco from LA, NYC, Seattle, etc. just to work at Magnolia, SpaceX, Baylor, and some big churches in town, such as Antioch.

Message me if you want access to some of the best deals in town.  

He's a major hard money lender in town and has a fairly simple process to get quick funding.

I am just exploring the possibility of this HELOC option.

To convert STR to LTR, evaluate rental comps, hire a property management company, explore multifamily properties in strong markets, and use a 5% Fannie Mae loan to buy a multifamily property.Good luck!