But if you need more cash in hand now and can handle the higher fees and reduced cash flow, option 1 could make sense.As for shopping around, it might be worth getting a few more quotes, especially if you think you can find something that combines the best of both worlds—a decent LTV and lower fees.Hope this helps!

The loss is typically treated as a short-term capital loss, which can directly offset short-term capital gains, and up to $3,000 of any excess loss can offset other income.Consult a tax professional to ensure you're handling this correctly and maximizing your potential tax benefits.However, if you lose the money you pay to buy the debt, the deduction from the loss doesn't equate to tax savings dollar for dollar. 

If it was me I would allow the tenant to handle the situation, but since you are asking the question, I would say an addendum is probably a good idea either direction you decide to go in, just so it's clearly spelled out to everyone.

For the syndicators that also offer mentorship, who on the syndication side handles the items you need help with?  

How do they handle future capital improvements?  

Once time becomes the burden, couldn't you contract directly with a handyman, plumber, electrician, etc to handle those tasks?

And for the record, banks handling HELOCs differently in different places doesn’t disprove the concept.

I have a good property manager that essentially handles everything for me.

You need to find a brokerage that specializes in LTR's and can also handle the property management.

But a vacation rental, you'd better be ready to take calls and handle things at the most inopportune times.