Mainly, because structural issues can be a complete black hole of money, time, effort--and it can be very difficult (and costly) to anticipate just how much money, time, and effort they'll consume.First, you'll need to figure out what's causing the structural issues--it could be settlement at the footers caused by ground water, it could be wood rot or termites in a beam, it could be masonry degradation caused by water coming off the roof, it could be improper drainage of the roof, it could be tree roots degrading the foundation, it could be a plumber who cut out a critical joist to install a line 20 years ago, it could be improper construction, it could be any or all of those things, and it could be any number of other potential causes.

I am spinning my wheels in my market.  

Ect. with the marketing spin put on it to make it sell(and more confusing). 

Obviously, lowering the fee and raising the rate is an option but that feels a little bit like spinning my wheels.At some point, if I'm dropping my rates far enough to compensate for a high cleaning fee, we get into the conversation of "is it even worth it to rent it at this rate and risk property damage, 4 star review, etc".

If the goal is money now, you need to make sure whatever you invest in is outpacing the interest on the HELOC otherwise you’re only spinning your wheels.  

Far better to think of CSAT as a flywheel you're trying to keep spinning over time to secure repeat bookings from guests you build a relationship with over time.  4.

Thinking through the tax implications, how that changes each deals numbers, and how we'd structure those payments has my head spinning.  

Their agenda is to keep the attendees off balance so that by the end of the presentation the attendee's head is spinning with "10X" and "millions of dollars" and whatever, so that $25,000 sounds like a small number.

The financing options I have seen that make the most sense are Construction to Permanent Loans, but researching all of the different loan options has my head spinning.

you're just swapping a rental payment for a mortgage payment to build equity.yes, you can try to spin up off market leads; it takes a lot of work.