Subject to seems to be more ideal to avoid any confusion over ownership, but it sounds like a pretty involved process that could cost time and money (whereas the other approach is free and simple).Any insights/advice would be appreciated!

Personally, we're okay with properties that cashflow decently, but have long term appreciation upside too.

If I own A duplex and lease it to a management company that rents it out as a short term vacation rental there is no UBIT?

So, again, don't take their track record over the last few months, in terms of investor returns.  

Regular financing is still an option but if any of you have some thoughts on what terms make sense, I'd love to hear them.

This one is more recommended if you are thinking of doing a flip or a temporary investment since it doesnt have long term effects like the refinance. 

Purchase price: $71,000 Sale price: $275,000 single family home bought and used as a long term rental. switched to STR and held for a few more years before selling to another investor What made you interested in investing in this type of deal?

Hello BP,I live in a region with a handful of Short term rentals and I’m currently analyzing a property with STR potential.

Purchase price: $70,000 used as a mid term rental..

I moved home to California and turned it into a short to mid term rental.