Associations must now conduct a Structural Integrity Reserve Study (SIRS) to ensure they have adequate funds for necessary repairs and maintenance.

Poor managers fail to make repairs(or insist on them to owners), fail to followup on cleaners and fail take care of guests, therefore the reviews tank impacting bookings/ADR.

At these numbers HVAC repair breaks down to $2000 cost per year on average to replace a $10k unit every 5 years. 

And got the upper/lower water damage fixed and repaired. 

Hey Ryan, yes I was told that just a cleaning alone, not any repairs, would be around $200-$250 but was shocked when I was sent an itemized bill and was charged $550 to clean a 2BR/2B condo downtown.

And I know cashflow isn't everything in the beginning an can come with time, but I don't want to acquire a bunch of properties where I'm only going to net 100 / mo after PITI, because with those margins all it takes is one repair to wipe everything. 

The questions agents get from buyers and sellers may seem basic and even downright silly at times but that makes sense.I could try to fix my car myself but there's a large upfront cost of learning the relevant knowledge, buying tools/parts to make the repair, and the time spent in trial in error.

With a few of our STRs being glamping tents and RV sites, the cost of a policy to cover a the repair/replacement of a tent or picnic table is not worth it in my opinion.

Hypothetically if I win a bid, then would I be able to utilize a HML for any possible repairs now that they'd have access to inside the property?

To build that kind of portfolio you will also need help with financing, locating, inspecting, repairing, etc.