I want to point out something about what @Theresa Holl said.All those things are very cool and would be nice to offer, but they would constitute significant services which will change your taxable status.So you really have to balance those sorts of special experiences or offerings.

I think you equally partially answered that question, telling the difficulties you are facing with STR regulations.this is my prescription and what I have decided to do .consider HELOC your current property, use the money to 1- add some value to your current home if room provide ( not to exceed X $ amount) you can then rent out the extra created meat to help pay HELOC2- Use the balance of HELOC to purchase another home in an appreciating market and if possible one that allows STR. use cash flow from new property still towards HELOC and just allow second home appreciate OR if you can fine a fixer upper to do BRRRR tat will even be better.that is what I have resolved to to. you can get back to me at 301-256-1578 so we can continue to brainstorm.little cent

Would the tax benefits of writing it off as an expense just be balanced out by having to pay tax on it on the receiving (PM) side?

Over our 10+ years in the industry we have seen data that there is an almost unlimited high-end profit margin, but we also feel there is a relatively untapped and large inventory of lower profit flips available that most investors are not focusing on (that have multiple risk mitigation measures in place as well).Our goal is to find the balance of profit, risk, and consistency.

Maybe finding a balance between cash and financing could be the best approach here.

There is a primary outstanding mortgage on it (unknown outstanding balance, terms, etc.).

If she wanted cash in addition to refinancing the current loan balance you could also look at getting a HELOC on the property if you have sufficient equity to pay her back her portion of the equity owed.

Sometimes, it is better to pay the tax and put the money in something besides real estate if that gives you a balanced portfolio. 

It helps them clear their past due balance and often times they pay several months into the future too.

I explained I dont go to Indy in February and look at our balance sheet we have 20 projects going there..